Water → HCID 15294977, compound

HRID 2259217Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)=[O:12])=[C:9]([CH:28]3[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]3)[S:8][C:7]=2[CH:35]=1.[BH4-].[Na+].O>CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:15][CH:14]=3)=[O:12])=[C:9]([CH:28]3[CH2:29][CH2:30][CH:31]([OH:34])[CH2:32][CH2:33]3)[S:8][C:7]=2[CH:35]=1

Participants

Conditions

Temperature: 0 °C

Procedure

50 mg of [6-methoxy-2-(4-oxocyclohexyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone was dissolved in 4 ml of methanol and 0.5 ml of THF, followed by ice cooling, 6 mg of sodium borohydride was added, and the mixture was stirred at 0° C. for 15 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1) to obtain 32 mg of [6-methoxy-2-(4-hydroxycyclohexyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone.

Workup

additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off
customThe resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1)

Sources & evidence

ORD record: ord-c515a9422f9e4923ab4707d152580271
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05472962

Reaction notes

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