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Preparation of 3-pyrrolidinols by reduction of 3,4-epoxypyrrolidines

Preparation of 3-pyrrolidinols by reduction of 3,4-epoxypyrrolidines. Muraoka, Hideo; Sato, Haruyo (Toray Industries, Inc., Japan). Jpn. Kokai Tokkyo Koho JP 2002053551 A2 19 Feb 2002, 4 pp. (Japanese). (Japan). CODEN: JKXXAF. CLASS: ICM: C07D207-12. ICS: C07D487-08. APPLICATION: JP 2000-243298 10 Aug 2000. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) 3-Pyrrolidinols I [R = H, lower alkyl, alkenyl, (un)substituted Ph, arylalkyl, arylalkenyl; Ar = (un)substituted phenyl], useful as intermediates for drugs, etc., are prepd. in high selectivity by reducing 3,4-epoxypyrrolidines II (R, Ar = same as in I). A THF soln. of 1-benzyl-3,4-epoxypyrrolidine was treated with LiAlH4 at room temp. for 5 h to give 87.0% 1-benzyl-3-pyrrolidinol.

Samarium Diiodide Promoted Generation and Asymmetric Hydroxyalkylation of N,O-Diprotected (3S)-3-Pyrrolidinol 2-Carbanions

Samarium Diiodide Promoted Generation and Asymmetric Hydroxyalkylation of N,O-Diprotected (3S)-3-Pyrrolidinol 2-Carbanions. Zheng, Xiao; Feng, Chen-Guo; Ye, Jian-Liang; Huang, Pei-Qiang ( Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, Peop. Rep.In this article, certain chemicals are used. One of their cas registry numbers is 4298-08-2 China).Several reagents such as 4298-08-2 is used here. Organic Letters, 7(4), 553-556 (English) 2005 American Chemical Society. CODEN: ORLEF7. ISSN: 1523-7060. DOCUMENT TYPE: Journal CA Section: 31 (Alkaloids) The N,O-diprotected chiral nonracemic 2-pyridyl 3-pyrrolidinol-2-yl sulfide I undergoes efficient SmI2-mediated redn. to give the N,O-diprotected 3-pyrrolidinol 2-carbanion intermediate II, which reacted under Barbier-type conditions with ketones and aldehydes to afford the protected N-a-hydroxyalkyl-3-pyrrolidines III [R1R2 = (CH2)5, (CH2)4; R1 = R2 = Me; R1 = Et, R2 = Me; R1 = H, R2 = n-Pr, CHMe2] with excellent diastereoselectivity at the newly formed chiral center in the pyrrolidine ring. Application of the present method led to the formal asym. syntheses of (2R,3S)-2-hydroxymethyl-3-pyrrolidinol and (2S,3S)-3-hydroxyproline. ..