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Volumn , Issue 2, 2008, Pages 294-296

Efficient N-tert-butoxycarbonylation of indoles with di-tert-butyl dicarbonate catalyzed by cesium fluoride

Author keywords

Catalysis; Cesium fluoride; Di tert butyl dicarbonate; Indoles; Protecting groups

Indexed keywords

BICARBONATE; BUTYL 3 [3 (TERT BUTYLDIMETHYLSILANYLOXY)BUTYL]INDOLE 1 CARBOXYLATE; CESIUM; FLUORIDE; INDOLE DERIVATIVE; TERT BUTYL 3 (3 HYDROXYBUTYL) INDOLE 1 CARBOXYLATE; TERT BUTYL 3 [2 ACETYLAMINO 2 (METHOXYCARBONYL)ETHYL]INDOLE 1 CARBOXYLATE; TERT BUTYL 3 FORMYLINDOLE 1 CARBOXYLATE; TERT BUTYL 7 METHYLINDOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

EID: 38849194665     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000869     Document Type: Article
Times cited : (22)

References (17)
  • 6
    • 20444431969 scopus 로고    scopus 로고
    • For recent examples using this protocol for the N-tert-butoxycarbonylation of indoles, see: (d) Baran, P. S.; Shenvi, R. A.; Mitsos, C A. Angew. Chem. Int. Ed. 2005, 44, 3714.
    • For recent examples using this protocol for the N-tert-butoxycarbonylation of indoles, see: (d) Baran, P. S.; Shenvi, R. A.; Mitsos, C A. Angew. Chem. Int. Ed. 2005, 44, 3714.
  • 9
    • 0001686462 scopus 로고    scopus 로고
    • 3: Hasan, I.; Marinelli, E. R.; Lin, L.-C. C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157.
    • 3: Hasan, I.; Marinelli, E. R.; Lin, L.-C. C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157.
  • 10
    • 38849181194 scopus 로고    scopus 로고
    • 5: Dhanak, D.; Reese, C. B. J. Chem. Soc., Perkin Trans. 1 1986, 2181.
    • 5: Dhanak, D.; Reese, C. B. J. Chem. Soc., Perkin Trans. 1 1986, 2181.
  • 13
    • 38849084124 scopus 로고    scopus 로고
    • CsF was the best catalyst among the cesium salts examined under the identical conditions: CsCl (0%), CsBr (6%), CsI (0%).
    • CsF was the best catalyst among the cesium salts examined under the identical conditions: CsCl (0%), CsBr (6%), CsI (0%).
  • 14
    • 38849107737 scopus 로고    scopus 로고
    • 10
    • 10
  • 15
    • 0000081048 scopus 로고    scopus 로고
    • CsF-promoted desilylation of tert-butyldimethylsilyl ethers was reported: Cirillo, P. F.; Panek, J. S. J. Org. Chem. 1990, 55, 6071.
    • CsF-promoted desilylation of tert-butyldimethylsilyl ethers was reported: Cirillo, P. F.; Panek, J. S. J. Org. Chem. 1990, 55, 6071.
  • 16
    • 38849155332 scopus 로고    scopus 로고
    • Purchased from Mitsuwa Chemicals Co, Ltd
    • Purchased from Mitsuwa Chemicals Co., Ltd.
  • 17
    • 38849209352 scopus 로고    scopus 로고
    • The selected spectroscopic data are shown as follows: tert-Butyl 3-Formylindole-1-carboxylate: 1H NMR (CDCl3, δ, 1.71 (s, 9 H, 7.38 (t, J, 8.3 Hz, 1 H, 7.42 (t, J, 8.3 Hz, 1 H, 8.15 (d, J, 8.3 Hz, 1 H, 8.24 (s, 1 H, 8.29 (d, J, 8.3 Hz, 1 H, 10.11 (s, 1 H, 13C NMR (CDCl3, δ, 28.0, 85.6, 115.1, 121.5, 122.1, 124.6, 126.0, 126.1, 135.9, 136.4, 148.8, 185.7. tert-Butyl 7-Methylindole-1- carboxylate: 1H NMR (CDCl3, δ, 1.63 (s, 9 H, 2.64 (s, 3 H, 6.53 (d, J, 4.0 Hz, 1 H, 7.09 (d, J, 7.6 Hz, 1 H, 7.14 (t, J, 7.6 Hz, 1 H, 7.38 (d, J, 7.6 Hz, 1 H, 7.51 (d, J, 4.0 Hz, 1 H, 13C NMR (CDCl3, δ, 22.1, 28.0, 83.2, 107.3, 118.5, 123.1, 125.3, 127.5, 128.0, 131.9, 134.7, 149.5. tert- Butyl 3-[3-(tert-Butyldimethylsilanyloxy) butyl]indole-1-c
    • 3): δ = 21.0, 23.5, 28.1, 38.4, 67.4, 83.2, 115.1, 118.9, 120.7, 122.2, 124.2, 130.6, 135.5, 149.7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.