The direct preparation of protected hydrazines from alcohols via Mitsunobu chemistry

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4327-4330

  Di Grandi, Martin J ^a,b   Tilley, Jefferson W ^a  

^a HOFFMANN LA ROCHE INC   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ESTER; HYDRAZINE DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROGENATION; PURIFICATION; REACTION ANALYSIS; SOLUBILITY;

EID: 0029883036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00837-4     Document Type: Article

References (24)

1. Post-doctoral fellow 1991-1992; current address: Wyeth-Ayerst Research, Pearl River, NY, 10965.
2. Manna, S.; Falck, J. R. Syn. Comm. 1985, 15, 663-668.
3. Mitsunobu, O. Synthesis 1981, 1-28.
4. For mechanistic investigations of the Mitsunobu reaction see: Pautard-Cooper, A.; Evans, S. A. J. Org. Chem. 1989, 54, 2485-2488; Crich, D.; Dyker, H.; Harris, R. J. J. Org. Chem. 1989, 54, 257-259; Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487-6491; Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235-4238.
5. For mechanistic investigations of the Mitsunobu reaction see: Pautard-Cooper, A.; Evans, S. A. J. Org. Chem. 1989, 54, 2485-2488; Crich, D.; Dyker, H.; Harris, R. J. J. Org. Chem. 1989, 54, 257-259; Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487-6491; Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235-4238.
6. For mechanistic investigations of the Mitsunobu reaction see: Pautard-Cooper, A.; Evans, S. A. J. Org. Chem. 1989, 54, 2485-2488; Crich, D.; Dyker, H.; Harris, R. J. J. Org. Chem. 1989, 54, 257-259; Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487-6491; Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235-4238.
7. For mechanistic investigations of the Mitsunobu reaction see: Pautard-Cooper, A.; Evans, S. A. J. Org. Chem. 1989, 54, 2485-2488; Crich, D.; Dyker, H.; Harris, R. J. J. Org. Chem. 1989, 54, 257-259; Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487-6491; Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235-4238.
8. A literature search revealed two closely related transformations. The first reported the synthesis of diethyl N-allyl hydrazinedicarboxylate en route to phosphate esters, see: Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Japan 1967, 40, 935-939. The second report describes the synthesis of N-glycosyl-1,2-hydrazinedicarboxylates, see: Grynkiewicz, G.; Jurczak, J. Carbohyd. Res. 1975, 43, 188-191. Weinreb and others report the alkylation of DEAD under Mitsunobu conditions as a byproduct (18 %) in: Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709-5712. For the alkylation of glycine amides under Mitsunobu conditions, see Talaga, P.; Konig, W. Tetrahedron Lett. 1992, 33, 609-610.
9. A literature search revealed two closely related transformations. The first reported the synthesis of diethyl N-allyl hydrazinedicarboxylate en route to phosphate esters, see: Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Japan 1967, 40, 935-939. The second report describes the synthesis of N-glycosyl-1,2-hydrazinedicarboxylates, see: Grynkiewicz, G.; Jurczak, J. Carbohyd. Res. 1975, 43, 188-191. Weinreb and others report the alkylation of DEAD under Mitsunobu conditions as a byproduct (18 %) in: Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709-5712. For the alkylation of glycine amides under Mitsunobu conditions, see Talaga, P.; Konig, W. Tetrahedron Lett. 1992, 33, 609-610.
10. A literature search revealed two closely related transformations. The first reported the synthesis of diethyl N-allyl hydrazinedicarboxylate en route to phosphate esters, see: Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Japan 1967, 40, 935-939. The second report describes the synthesis of N-glycosyl-1,2-hydrazinedicarboxylates, see: Grynkiewicz, G.; Jurczak, J. Carbohyd. Res. 1975, 43, 188-191. Weinreb and others report the alkylation of DEAD under Mitsunobu conditions as a byproduct (18 %) in: Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709-5712. For the alkylation of glycine amides under Mitsunobu conditions, see Talaga, P.; Konig, W. Tetrahedron Lett. 1992, 33, 609-610.
11. A literature search revealed two closely related transformations. The first reported the synthesis of diethyl N-allyl hydrazinedicarboxylate en route to phosphate esters, see: Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Japan 1967, 40, 935-939. The second report describes the synthesis of N-glycosyl-1,2-hydrazinedicarboxylates, see: Grynkiewicz, G.; Jurczak, J. Carbohyd. Res. 1975, 43, 188-191. Weinreb and others report the alkylation of DEAD under Mitsunobu conditions as a byproduct (18 %) in: Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709-5712. For the alkylation of glycine amides under Mitsunobu conditions, see Talaga, P.; Konig, W. Tetrahedron Lett. 1992, 33, 609-610.
12. 2-; 40 %). Falck's procedure stipulated that the azodicarboxylate and TPP were to be premixed for twenty minutes prior to the addition of any other reagents. When this was done in DMF, two molecules of phosphine adduct i react to generate species ii which then reacts further to afford iv. That this is a competitive pathway for adduct i is evidenced by the 60:40 mixture of iii and iv produced. matrix presented
13. 4, filtered and concentrated in vacuo. Purification of the crude product on silica gel, eluting with EtOAc:Hex gave protected hydrazine 4. All new compounds gave satisfactory spectral and microanalytical data.
14. Gennari, C.; Colombo, L.; Bertolini, G.; J. Am. Chem. Soc. 1986, 108, 6394-6395; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395-6397; Trimble, L.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108, 6397-6399; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525-5540.
15. Gennari, C.; Colombo, L.; Bertolini, G.; J. Am. Chem. Soc. 1986, 108, 6394-6395; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395-6397; Trimble, L.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108, 6397-6399; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525-5540.
16. Gennari, C.; Colombo, L.; Bertolini, G.; J. Am. Chem. Soc. 1986, 108, 6394-6395; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395-6397; Trimble, L.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108, 6397-6399; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525-5540.
17. Gennari, C.; Colombo, L.; Bertolini, G.; J. Am. Chem. Soc. 1986, 108, 6394-6395; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395-6397; Trimble, L.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108, 6397-6399; Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. Tetrahedron 1988, 44, 5525-5540.
18. For an interesting application of α-hydrazine esters to peptide chemistry, see: Lecoq, A.; Marraud, M.; Aubry, A. Tetrahedron Lett. 1991, 32, 2765-2768.
19. Di-t-butylhydrazinedicarboxylates have been converted into amines in one pot with acid and hydrogen, see: Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765-6768; Oppolzer, W.; Moretti, R. Helv. Chim. Acta 1986, 69, 1923-1926.
20. Di-t-butylhydrazinedicarboxylates have been converted into amines in one pot with acid and hydrogen, see: Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765-6768; Oppolzer, W.; Moretti, R. Helv. Chim. Acta 1986, 69, 1923-1926.
21. Substituted ethyl-1,2-hydrazinedicarboxylates have been converted to carboethoxyamines, see: Taylor, E. C.; Sowinski, F. J. Org. Chem. 1974, 39, 907-910.
22. The hydrogenation product gave an identical NMR spectrum to that of an authentic sample prepared from methyl 3-phenylpropanoate, LDA, and DBAD.
23. Mandelate esters gave products that decomposed on exposure to silica gel precluding identification.
24. The crude product mixture of these reactions was contaminated with substantial amounts of TPP whereas in the examples in Table 1 little or no TPP was found.