Enzymatic preparation of optically active 1-benzyl-3-hydroxypyrrolidines

Enantiomer

Volumn 2, Issue 3-4, 1997, Pages 311-314

  Hasegawa, Junzo ^a   Sawa, Ikuo ^a   Mori, Natsuki ^a   Kutsuki, Hidetoshi ^a   Ohashi, Takehisa ^a  

^a KANEKA CORPORATION   (Japan)

Author keywords

1 Benzyl 3 hydroxypyrrolidine; 3 Hydroxypyrrolidine; Enan tioselectivity; Enzyme; Lipase

Indexed keywords

PYRROLIDINE DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030837660     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (10)

1. Ueno, T., Iuchi, K., Kawahata, Y. and Tsukamoto, G. (1987). J. Heterocycl. Chem., 24, 1025.
2. Shibata, T., Iino, K. and Sugimura, Y. (1986). Heterocycles, 24, 1331.
3. Tamazawa, K., Arima, H., Kojima, T., Isomura, Y., Okada, M., Fujita, S., Furuya, T., Takenaka, T., Inagaki, O. and Terai, M. (1986). J. Med. Chem., 29, 2504.
4. Bhat, K. L., Flanagan, D. M. and Joullie, M. M. (1985). Synth. Commun., 15, 587.
5. Harris, B. D., Bhat, K. L. and Joullie, M. M. (1986). Synth. Commun., 16, 1815.
6. Hashimoto, M., Eda, Y., Osanai, Y., Iwai, T. and Aoki, S. (1986). Chem. Lett., 8937.
7. Brown, H. C., Prasad, J. V. N. V. and Gupta, A. K. (1986). J. Org. Chem., 51, 4296.
8. 3, 90 MHz) 5 0.87 (3H, t), 1.28 (2H × 4, m), 1.60 (2H, m), 2.27 (2H, t), 1.60-2.92 (3H × 3, m), 3.63 (2H, s), 6.19 (1H, m), 7.30 (5H, s); bp 180°C/3 Torr.
9. The enantiomeric excesses of (R)-5b-d and (S)-4b-d and the optical purities of (R)-5a and (S)-4a were estimated as follows: (R)-4a-d were hydrolyzed to (R)-5a-d under alkaline conditions, and then (R)- and (S)-5b-d were converted to the corresponding N-phenyl-carbamates; which were subjected to HPLC analyses (column, Chiralcel OD, hexane/2-propanol/isopropylamine (80/20/0.1 by volume); flow rate, 1.5 ml/min; detection, 254 run). Optical purities of (R)-5a and (S)-4a were estimated by comparison of their specific rotations with those of (R)-5a and (R)-4a, which were prepared from optically pure (R)-3-hydroxypyrrolidine.
10. Horiguchi, A. and Mochida, K. (1995). Biosci. Biotech. Biochem., 59, 1287.