Lithium borohydride → (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol

HRID 409034

Reaction equation

[BH4-].[Li+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:21][CH2:20][C@@H:19]([O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]1=[O:33]>COC1CCCC1>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:21][CH2:20][C@@H:19]([O:22][Si:23]([CH:27]([CH3:29])[CH3:28])([CH:30]([CH3:32])[CH3:31])[CH:24]([CH3:25])[CH3:26])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C@H:12]1[OH:33]

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium borohydride (0.982 g, 45.1 mmol) was added to a cyclopentyl methyl ether (30 mL) solution of (6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (5.0224 g, 11.27 mmol) at 0° C. under N2. The reaction mixture was stirred at 0° C. for 2 hours and then an addition 4 hours at room temperature. The reaction was quenched by adding methanol. The reaction mixture was stirred for 0.5 hour. The solvent was mostly removed via vacuum and the crude material was taken up in ethyl acetate, which was washed with water three times. Flash column by ethyl acetate in hexane from 0 to 10% gave the desired product (3.28 g, 65%).

Workup

additionan addition 4 hours at room temperature
customThe reaction was quenched
additionby adding methanol
stirringThe reaction mixture was stirred for 0.5 hour
customThe solvent was mostly removed via vacuum
washwhich was washed with water three times

Sources & evidence

ORD record: ord-613adbb88c844232aca16582d503ae0a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759372B2

Linked notes

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