Water → [(2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidin-2-yl]methanol

HRID 1436153Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([C@H:16]2[NH:20][C@@H:19]([C:21](OCC)=[O:22])[CH2:18][CH2:17]2)[CH:11]=[C:12]([F:15])[C:13]=1[F:14].O.[OH-].[Na+]>C1COCC1>[F:15][C:12]1[CH:11]=[C:10]([C@H:16]2[NH:20][C@@H:19]([CH2:21][OH:22])[CH2:18][CH2:17]2)[CH:9]=[C:8]([F:7])[C:13]=1[F:14]

Participants

Conditions

Temperature: -15 °C

Procedure

LAH (483 mg) was added to a solution of ethyl (2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-carboxylate (2.91 g) in THF (50 mL) at −15° C. over one hour. The reaction solution was stirred at −15° C. for 19 hours. Water (0.5 mL), a 5 N sodium hydroxide solution (0.5 mL), and water (1.5 mL) were sequentially added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 2.4 g of the title compound. The property values of the compound are as follows.

Workup

stirringthe mixture was stirred at room temperature for 30 minutes
filtrationThe reaction solution was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-a6df310f347b4e6899b2cf76e84dcebc
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618960B2

Reaction notes

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