Lithium borohydride → HCID 71009034, compound

HRID 1626092Notes

Reaction equation

[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@@H:9]1[C@@:11]([CH3:27])([NH:20][S@@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[C:12]([C:15](OCC)=[O:16])([F:14])[F:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>>[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@@H:9]1[C@@:11]([CH3:27])([NH:20][S@@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[C:12]([F:13])([F:14])[CH2:15][OH:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 4148881Lithium borohydride

HCID 71009168HCID 71009168, compound

Product 1

HCID 71009034HCID 71009034, compoundYield 80%

Procedure

Starting from (1S,2S)-2-[(R)-2-ethoxycarbonyl-2,2-difluoro-1-methyl-1-((R)-2-methyl-propane-2-sulfinylamino)-ethyl]-cyclopropanecarboxylic acid tert-butylester (intermediate J3.3) the reduction with lithium borohydride yielded the (1S,2S)-2-[(R)-2,2-difluoro-3-hydroxy-1-methyl-1-((R)-2-methyl-propane-2-sulfinylamino)-propyl]-cyclopropanecarboxylic acid tert-butyl ester (80% yield) as a white solid. MS (ISP): m/z=370.2 [M+H]+.

Sources & evidence

ORD record: ord-0c5fa550ad464ddabe410f75ed8b1d0b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785436B2

Reaction notes

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