Two useful methods for the preparation of (R)- and (S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)ethanamine

Tetrahedron Asymmetry

Volumn 8, Issue 15, 1997, Pages 2613-2618

  De Sousa, Simon E ^a   O'Brien, Peter ^a   Poumellec, Pierre ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030738669     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00277-2     Document Type: Article

References (28)

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4. O'Brien, P.; Poumellec, P. Tetrahedron Lett., 1996, 37, 8057-8058.
5. For a review entitled "Enantioselective Desymmetrisation of Achiral Epoxides", see: Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron, 1996, 52, 14361-14384.
6. Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem., 1991, 34, 181-189. See also: Chang, A.-C.; Takemori, A. E.; Ojala, W. H.; Gleason, W. B.; Portoghese, P. S. J. Med. Chem., 1994, 37, 4490-4498; Weerawarna, S. A.; Davis, R. D.; Nelson, W. L. J. Med. Chem., 1994, 37, 2856-2864.
7. Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem., 1991, 34, 181-189. See also: Chang, A.-C.; Takemori, A. E.; Ojala, W. H.; Gleason, W. B.; Portoghese, P. S. J. Med. Chem., 1994, 37, 4490-4498; Weerawarna, S. A.; Davis, R. D.; Nelson, W. L. J. Med. Chem., 1994, 37, 2856-2864.
8. Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem., 1991, 34, 181-189. See also: Chang, A.-C.; Takemori, A. E.; Ojala, W. H.; Gleason, W. B.; Portoghese, P. S. J. Med. Chem., 1994, 37, 4490-4498; Weerawarna, S. A.; Davis, R. D.; Nelson, W. L. J. Med. Chem., 1994, 37, 2856-2864.
9. Ito; F. (Pfizer Inc.) JP-00820, 1996 (Chem. Abst., 1996, 125, 86487y).
10. Ito; F. (Pfizer Inc.) JP-00820, 1996 (Chem. Abst., 1996, 125, 86487y).
11. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron, 1993, 49, 965-986.
12. Significant levels of racemisation can occur in the reaction of N-protected phenylglycine (R)-3 with pyrrolidine to give (R)-4 when isobutyl chloroformate, 1,3-dicyclohexylcarbodiimide (DCC) or bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-C1) are used as the coupling reagent. After a careful study, Singh (see reference 3) demonstrated that racemisation could be prevented if DCC was used in combination with 1-hydroxybenzotriazole (HOBT) at low temperature.
13. In the reaction of N-protected phenylglycine (R)-3 with a range of amines, Koga has shown that racemisation can be prevented using diethylphosphorocyanidate-mediated coupling: Shirai, R.; Aoki, K.; Sato, D.; Kim, H.-D.; Murakata, M.; Yasukata, T.; Koga, K. Chem. Pharm. Bull., 1994, 42, 690-693.
14. O'Brien, P.; Poumellec, P. Tetrahedron Lett., 1996, 37, 5619-5622.
15. de Sousa, S. E.; O'Brien, P. Tetrahedron Lett., 1997, 38, 4885-4888.
16. Dieter, R. K.; Lagu, B.; Dieter, J. W.; Deo, N.; Pennington, W. T. Synlett, 1990, 109-110; Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W.; J. Org. Chem., 1992, 57, 1663-1671.
17. Dieter, R. K.; Lagu, B.; Dieter, J. W.; Deo, N.; Pennington, W. T. Synlett, 1990, 109-110; Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W.; J. Org. Chem., 1992, 57, 1663-1671.
18. Miao, G.; Rossiter, B. E. J. Org. Chem., 1995, 60, 8424-8427.
19. (R)-and (S)-styrene oxide are available from the Aldrich Chemical Company Ltd. (R)-Styrene oxide costs £32.50 per 5 g; (S)-styrene oxide costs £20.00 per 1 g.
20. BOH) and 3.54 (1 H, t, J 5.8, PhCHN).
21. The water is necessary otherwise the second step does not proceed efficiently.
22. Pirkle, W. H.; Hoover, D. J. Top. Stereochem., 1982, 13, 263-331.
23. The N,N-dialkylation route to amino alcohol 6 has been reported previously: Brown, E.; Penfornis, A.; Bayma, J.; Touet, J. Tetrahedron: Asymmetry, 1991, 2, 339-342; Brown, E.; Lézé, A.; Touet, J. Tetrahedron: Asymmetry, 1996, 7, 2029-2040. For other recent examples of N,N-dialkylation of amino alcohols, see: Fulton, D. A.; Gibson, C. L. Tetrahedron Lett., 1997, 38, 2019-2022; Juárez, J.; Gnecco, D.; Galindo, A.; Enríquez, R. G.; Marazano, C.; Reynolds, W. F. Tetrahedron: Asymmetry, 1997, 8, 203-206; Beaulieu, P. L.; Wernic, D. J. Org. Chem., 1996, 61, 3635-3645.
24. The N,N-dialkylation route to amino alcohol 6 has been reported previously: Brown, E.; Penfornis, A.; Bayma, J.; Touet, J. Tetrahedron: Asymmetry, 1991, 2, 339-342; Brown, E.; Lézé, A.; Touet, J. Tetrahedron: Asymmetry, 1996, 7, 2029-2040. For other recent examples of N,N-dialkylation of amino alcohols, see: Fulton, D. A.; Gibson, C. L. Tetrahedron Lett., 1997, 38, 2019-2022; Juárez, J.; Gnecco, D.; Galindo, A.; Enríquez, R. G.; Marazano, C.; Reynolds, W. F. Tetrahedron: Asymmetry, 1997, 8, 203-206; Beaulieu, P. L.; Wernic, D. J. Org. Chem., 1996, 61, 3635-3645.
25. The N,N-dialkylation route to amino alcohol 6 has been reported previously: Brown, E.; Penfornis, A.; Bayma, J.; Touet, J. Tetrahedron: Asymmetry, 1991, 2, 339-342; Brown, E.; Lézé, A.; Touet, J. Tetrahedron: Asymmetry, 1996, 7, 2029-2040. For other recent examples of N,N-dialkylation of amino alcohols, see: Fulton, D. A.; Gibson, C. L. Tetrahedron Lett., 1997, 38, 2019-2022; Juárez, J.; Gnecco, D.; Galindo, A.; Enríquez, R. G.; Marazano, C.; Reynolds, W. F. Tetrahedron: Asymmetry, 1997, 8, 203-206; Beaulieu, P. L.; Wernic, D. J. Org. Chem., 1996, 61, 3635-3645.
26. The N,N-dialkylation route to amino alcohol 6 has been reported previously: Brown, E.; Penfornis, A.; Bayma, J.; Touet, J. Tetrahedron: Asymmetry, 1991, 2, 339-342; Brown, E.; Lézé, A.; Touet, J. Tetrahedron: Asymmetry, 1996, 7, 2029-2040. For other recent examples of N,N-dialkylation of amino alcohols, see: Fulton, D. A.; Gibson, C. L. Tetrahedron Lett., 1997, 38, 2019-2022; Juárez, J.; Gnecco, D.; Galindo, A.; Enríquez, R. G.; Marazano, C.; Reynolds, W. F. Tetrahedron: Asymmetry, 1997, 8, 203-206; Beaulieu, P. L.; Wernic, D. J. Org. Chem., 1996, 61, 3635-3645.
27. The N,N-dialkylation route to amino alcohol 6 has been reported previously: Brown, E.; Penfornis, A.; Bayma, J.; Touet, J. Tetrahedron: Asymmetry, 1991, 2, 339-342; Brown, E.; Lézé, A.; Touet, J. Tetrahedron: Asymmetry, 1996, 7, 2029-2040. For other recent examples of N,N-dialkylation of amino alcohols, see: Fulton, D. A.; Gibson, C. L. Tetrahedron Lett., 1997, 38, 2019-2022; Juárez, J.; Gnecco, D.; Galindo, A.; Enríquez, R. G.; Marazano, C.; Reynolds, W. F. Tetrahedron: Asymmetry, 1997, 8, 203-206; Beaulieu, P. L.; Wernic, D. J. Org. Chem., 1996, 61, 3635-3645.
28. 2O) for the reduction: Tschantz, M. A.; Burgess, L. E.; Meyers, A. I. Org. Synth., 1996, 73, 221-230.