메뉴 건너뛰기




Volumn 73, Issue 9, 2008, Pages 3662-3665

Concise synthesis of (S)-N-BOC-2-hydroxymethylmorpholine and (S)-N-BOC-morpholine-2-carboxylic acid

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; SYNTHESIS (CHEMICAL);

EID: 43449131247     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800356q     Document Type: Article
Times cited : (20)

References (43)
  • 1
    • 43449133684 scopus 로고    scopus 로고
    • Fish, P. V.; Mackenny, M. C.; Stobie, A.; Wakenhut, F.; Whitlock, G. A. U.S. 2005/250775, Nov. 10, 2005; CAN 143:460166.
    • (a) Fish, P. V.; Mackenny, M. C.; Stobie, A.; Wakenhut, F.; Whitlock, G. A. U.S. 2005/250775, Nov. 10, 2005; CAN 143:460166.
  • 2
    • 43449130203 scopus 로고    scopus 로고
    • Fish, P. V.; Mackenny, M. C.; Stobie, A.; Wakenhut, F.; Whitlock, G. A WO 2005/105100, Nov. 10, 2005; CAN 143:460165.
    • (b) Fish, P. V.; Mackenny, M. C.; Stobie, A.; Wakenhut, F.; Whitlock, G. A WO 2005/105100, (Nov. 10, 2005; CAN 143:460165.
  • 3
    • 43449089892 scopus 로고    scopus 로고
    • Barta, N. S.; Glase, S. A.; Gray, D. L.; Reichard, G. A.; Simons, L. J.; Xu, WU.S. 2005/245519, Nov. 3, 2005; CAN 143:440426.
    • (c) Barta, N. S.; Glase, S. A.; Gray, D. L.; Reichard, G. A.; Simons, L. J.; Xu, WU.S. 2005/245519, Nov. 3, 2005; CAN 143:440426.
  • 4
    • 43449107802 scopus 로고    scopus 로고
    • Schelkun, R. M.; Yuen, P.-W. WO2006/056873, Jun. 1, 2006; CAN 145:27985.
    • Schelkun, R. M.; Yuen, P.-W. WO2006/056873, Jun. 1, 2006; CAN 145:27985.
  • 5
    • 43449106013 scopus 로고    scopus 로고
    • Ono, S.; Yamafuji, T.; Chaki, H.; Maekawa, M.; Todo, Y.; Narita, H. EP383281, Aug. 8, 1994; CAN 114:81222.
    • (a) Ono, S.; Yamafuji, T.; Chaki, H.; Maekawa, M.; Todo, Y.; Narita, H. EP383281, Aug. 8, 1994; CAN 114:81222.
  • 6
    • 43449115199 scopus 로고    scopus 로고
    • Carruthers, N. I.; Gomez, L. A.; Jablonowski, J. A.; Keith, J. M.; Letavic, M. A.; Ly, K. S.; Miller, J. M. B.; Stocking, E. M.; Wolin, R. LWO2006/066197, Jun. 22, 2006; CAN 145:83244.
    • (b) Carruthers, N. I.; Gomez, L. A.; Jablonowski, J. A.; Keith, J. M.; Letavic, M. A.; Ly, K. S.; Miller, J. M. B.; Stocking, E. M.; Wolin, R. LWO2006/066197, Jun. 22, 2006; CAN 145:83244.
  • 8
    • 43449132813 scopus 로고    scopus 로고
    • Baldwin, J. J.; Claremon, D. A.; Tice, C.; Cacatian, S.; Dillard, L. W.; Ishchenko, A. V.; Yuan, J.; Xu, Z.; McGeehan, G.; Zhao, W.; Simpson, R. D.; Singh, S. B.; Flaherty, P. T.; Wery, J.-P. WO2006/042150. Apr. 20, 2006; CAN 144:432692.
    • (a) Baldwin, J. J.; Claremon, D. A.; Tice, C.; Cacatian, S.; Dillard, L. W.; Ishchenko, A. V.; Yuan, J.; Xu, Z.; McGeehan, G.; Zhao, W.; Simpson, R. D.; Singh, S. B.; Flaherty, P. T.; Wery, J.-P. WO2006/042150. Apr. 20, 2006; CAN 144:432692.
  • 9
    • 43449128973 scopus 로고    scopus 로고
    • Ko, S. S.; Delucca, G. V.; Duncia, J. V.; Santella, J. B., III; Wacker, D. A. WO 2000/035877, Dec. 17, 2000; CAN 133:58720.
    • (b) Ko, S. S.; Delucca, G. V.; Duncia, J. V.; Santella, J. B., III; Wacker, D. A. WO 2000/035877, Dec. 17, 2000; CAN 133:58720.
  • 10
    • 43449094795 scopus 로고    scopus 로고
    • Ackerman, J.; Banner, D.; Gubernator, K.; Hadvary, P.; Hilpert, K.; Mueller, K.; Labler, L.; Schmid, G.; Tschopp, T. EP468231, July 2, 1991; CAN 116:214908.
    • (c) Ackerman, J.; Banner, D.; Gubernator, K.; Hadvary, P.; Hilpert, K.; Mueller, K.; Labler, L.; Schmid, G.; Tschopp, T. EP468231, July 2, 1991; CAN 116:214908.
  • 11
    • 43449123444 scopus 로고    scopus 로고
    • Amegadzie, A. K.; Beck, J. P.; Gardinier, K. M.; Hembre, E. J.; Ruble, J. C.; Savin, K. A.; Wakefield, B. DWO 2006/066174, June 22, 2006; CAN 145:83313.
    • (d) Amegadzie, A. K.; Beck, J. P.; Gardinier, K. M.; Hembre, E. J.; Ruble, J. C.; Savin, K. A.; Wakefield, B. DWO 2006/066174, June 22, 2006; CAN 145:83313.
  • 12
    • 43449126636 scopus 로고    scopus 로고
    • Bower, J. F.; Poyser, J. P.; Turner, P.; Waterson, D.; Winter, J. WO2006/067401, June 29, 2006; CAN 145:103720.
    • (e) Bower, J. F.; Poyser, J. P.; Turner, P.; Waterson, D.; Winter, J. WO2006/067401, June 29, 2006; CAN 145:103720.
  • 13
    • 43449106012 scopus 로고    scopus 로고
    • Gudmundsson, K.; Miller, J. F; Turner, E. M. WO20067020415. Feb. 23, 2006; CAN 144:233072.
    • (f) Gudmundsson, K.; Miller, J. F; Turner, E. M. WO20067020415. Feb. 23, 2006; CAN 144:233072.
  • 14
    • 43449138306 scopus 로고    scopus 로고
    • Fink, B. E.; Gavai, A. V.; Vite, G. D.; Chen, P.; Mastalerz, H.; Norris, D. J.; Tokarski, J. S.; Zhao, Y.; Han, W.-C. WO2005/066176, July 21, 2005; CAN 143:153408.
    • (g) Fink, B. E.; Gavai, A. V.; Vite, G. D.; Chen, P.; Mastalerz, H.; Norris, D. J.; Tokarski, J. S.; Zhao, Y.; Han, W.-C. WO2005/066176, July 21, 2005; CAN 143:153408.
  • 15
    • 43449120509 scopus 로고    scopus 로고
    • Gavai, A. V.; Han, W.-C.; Chen, P.; Ruediger, E. H.; Mastalerz, H.; Fink, B. E.; Norris, D. J. WO2005/065266, July 21, 2005; CAN 143:133402.
    • h) Gavai, A. V.; Han, W.-C.; Chen, P.; Ruediger, E. H.; Mastalerz, H.; Fink, B. E.; Norris, D. J. WO2005/065266, July 21, 2005; CAN 143:133402.
  • 16
    • 43449094467 scopus 로고    scopus 로고
    • Kato, S.; Yamazaki, H.; Hirokawa, Y.; Suga, Y.; Yoshida, N.; Morikage, Y.; Morikage, K.; Oku, S. JP2004/277319, Oct. 7, 2004; CAN 141:307556.
    • (i) Kato, S.; Yamazaki, H.; Hirokawa, Y.; Suga, Y.; Yoshida, N.; Morikage, Y.; Morikage, K.; Oku, S. JP2004/277319, Oct. 7, 2004; CAN 141:307556.
  • 17
    • 43449102606 scopus 로고    scopus 로고
    • Munson, M.; Mareska, D. A.; Kim, Y.; Groneberg, R. D.; Rizzi, J.; Rodriguez, M.; Kim, G.; Vigers, G.; Rao, C.; Balachari, D.; Harvey, D. US2004/192653, Sept. 30, 2004; CAN 141:314320.
    • (j) Munson, M.; Mareska, D. A.; Kim, Y.; Groneberg, R. D.; Rizzi, J.; Rodriguez, M.; Kim, G.; Vigers, G.; Rao, C.; Balachari, D.; Harvey, D. US2004/192653, Sept. 30, 2004; CAN 141:314320.
  • 18
    • 43449134501 scopus 로고    scopus 로고
    • Bhide, R.; Cai, Z.-w.; Qian, L.; Barbosa, S. WO2004/009784, Jan. 29, 2004; CAN 140:124558.
    • (k) Bhide, R.; Cai, Z.-w.; Qian, L.; Barbosa, S. WO2004/009784, Jan. 29, 2004; CAN 140:124558.
  • 19
    • 43449117887 scopus 로고    scopus 로고
    • Luckhurst, C.; Perry, M.; Sanganee, H.; Springthorpe, B. WO2003/078395, Sept. 25, 2003; CAN 139:276907.
    • (l) Luckhurst, C.; Perry, M.; Sanganee, H.; Springthorpe, B. WO2003/078395, Sept. 25, 2003; CAN 139:276907.
  • 20
    • 43449129572 scopus 로고    scopus 로고
    • Mastalerz, H.; Zhang, G.; Tarrant, J. G.; Vite, G. D. WO2003/042172, May 22, 2003; CAN 138:401758.
    • (m) Mastalerz, H.; Zhang, G.; Tarrant, J. G.; Vite, G. D. WO2003/042172, May 22, 2003; CAN 138:401758.
  • 21
    • 43449092976 scopus 로고    scopus 로고
    • Sanganee, H.; Springthorpe, B. WO2003/024962, Mar. 6, 2003; CAN 138:271690.
    • (n) Sanganee, H.; Springthorpe, B. WO2003/024962, Mar. 6, 2003; CAN 138:271690.
  • 22
    • 43449115494 scopus 로고    scopus 로고
    • Gustafsson, J.; Hossain, N.; Nilsson, S. WO2003/018576, Mar. 6, 2003; CAN 138:221591.
    • (o) Gustafsson, J.; Hossain, N.; Nilsson, S. WO2003/018576, Mar. 6, 2003; CAN 138:221591.
  • 23
    • 43449090206 scopus 로고    scopus 로고
    • Gustafsson, J.; Hossain, N.; Nilsson, S. WO2003/018566, Mar. 6, 2003; CAN138:221472.
    • (p) Gustafsson, J.; Hossain, N.; Nilsson, S. WO2003/018566, Mar. 6, 2003; CAN138:221472.
  • 24
    • 43449139256 scopus 로고    scopus 로고
    • Ko, S. S.; Delucca, G. V.; Duncia, J. V.; Santella, J. B., III; Wacker, D. A. WO2000/035877, June 22, 2000; CAN 133:58720.
    • (q) Ko, S. S.; Delucca, G. V.; Duncia, J. V.; Santella, J. B., III; Wacker, D. A. WO2000/035877, June 22, 2000; CAN 133:58720.
  • 25
    • 43449088335 scopus 로고    scopus 로고
    • Miyake, H.; Take, K.; Shigenaga, S.; Azami, H.; Sasaki, H.; Eikyu, Y.; Nakai, K.; Ishida, J.; Manabe, T.; Konishi, N.; Terasaka, T. WO98/57954, Dec. 22, 1998; CAN 130:81525.
    • (r) Miyake, H.; Take, K.; Shigenaga, S.; Azami, H.; Sasaki, H.; Eikyu, Y.; Nakai, K.; Ishida, J.; Manabe, T.; Konishi, N.; Terasaka, T. WO98/57954, Dec. 22, 1998; CAN 130:81525.
  • 26
    • 43449137670 scopus 로고    scopus 로고
    • Yanagisawa, H.; Fujimoto, K.; Shimoji, Y.; Kanezaki, T.; Iwata, N.; Kubo, Y. JP 04120021, 1992; CAN 117:251362.
    • (s) Yanagisawa, H.; Fujimoto, K.; Shimoji, Y.; Kanezaki, T.; Iwata, N.; Kubo, Y. JP 04120021, 1992; CAN 117:251362.
  • 27
    • 43449098263 scopus 로고    scopus 로고
    • Ackerman, J.; Banner, D.; Gubernator, K.; Hadvary, P.; Hilpert, K.; Mueller, K.; Labler, L.; Schmid, G.; Tschopp, T. EP468231, Jan. 29, 1992; CAN 116:214908.
    • (t) Ackerman, J.; Banner, D.; Gubernator, K.; Hadvary, P.; Hilpert, K.; Mueller, K.; Labler, L.; Schmid, G.; Tschopp, T. EP468231, Jan. 29, 1992; CAN 116:214908.
  • 28
    • 43449140116 scopus 로고    scopus 로고
    • Nilsson, M.; Zhou, X.-X.; Oden, L.; Classon, B.; Noren, R.; Grabowska, U.; Jackson, P.; Fallon, P.; Carr, A.; Liley, M.; Tozer, M.; Johnson, T.; Diaz, V.; Crespo, L.; Kangasmetsa, J.; Bonnaud, T. WO2005/066180, July 21,2005; CAN 143:153706.
    • (u) Nilsson, M.; Zhou, X.-X.; Oden, L.; Classon, B.; Noren, R.; Grabowska, U.; Jackson, P.; Fallon, P.; Carr, A.; Liley, M.; Tozer, M.; Johnson, T.; Diaz, V.; Crespo, L.; Kangasmetsa, J.; Bonnaud, T. WO2005/066180, July 21,2005; CAN 143:153706.
  • 30
    • 43449102008 scopus 로고    scopus 로고
    • The lowest bulk quote we received for (S)-3-amino-1,2-propanediol was 10 kg at $6000/kg).
    • The lowest bulk quote we received for (S)-3-amino-1,2-propanediol was 10 kg at $6000/kg).
  • 31
    • 43449088648 scopus 로고    scopus 로고
    • Ackerman, J.; Banner, D.; Gubernator, K.; Hadvary, P.; Hilpert, K.; Mueller, K.; Labler, L.; Schmid, G.; Tschopp, T. EP468231, Jan 29, 1992; CAN 116:214908.
    • Ackerman, J.; Banner, D.; Gubernator, K.; Hadvary, P.; Hilpert, K.; Mueller, K.; Labler, L.; Schmid, G.; Tschopp, T. EP468231, Jan 29, 1992; CAN 116:214908.
  • 34
    • 43449113073 scopus 로고    scopus 로고
    • (R)-Epichlorohydrin used for this study was purchased for $470/kg in 5 kg lots. Both enantiomers of epichlorohydrin are available in bulk for <$40/kg.
    • (R)-Epichlorohydrin used for this study was purchased for $470/kg in 5 kg lots. Both enantiomers of epichlorohydrin are available in bulk for <$40/kg.
  • 42
    • 43449105151 scopus 로고    scopus 로고
    • The HPLC purity of the isolated chlorohydrin had dropped from about 90 area % to less than 60% during storage.
    • The HPLC purity of the isolated chlorohydrin had dropped from about 90 area % to less than 60% during storage.
  • 43
    • 43449100164 scopus 로고    scopus 로고
    • Formation of the hemisuccinate 16 was confirmed by mass spectral data. Other anhydrides examined either gave sluggish reaction and poor selectivity (phthalic anhydride, glutaric anhydride) or poor partitioning during the aqueous base extractions (hexahydrophthalic anhydride).
    • Formation of the hemisuccinate 16 was confirmed by mass spectral data. Other anhydrides examined either gave sluggish reaction and poor selectivity (phthalic anhydride, glutaric anhydride) or poor partitioning during the aqueous base extractions (hexahydrophthalic anhydride).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.