Sodium borohydride → HCID 22878261, compound

HRID 1489208Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[OH:17])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 2-(4'-nitrobenzene)methylcyclohexan-1-one (44) in 5 mL of methanol at 0° C. was added portionwise sodium borohydride, and the reaction mixture was allowed to stir at 0° C. for 1.5 h before quenching with saturated aqueous NH4C1. The methanol was removed under diminished pressure, and the resultant aqueous residue was extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, and concentrated under diminshed pressure. Purification by flash column chromatography (silica gel, hexanes/ethyl acetate, 4:1) gave 10 mg (20%) of the desired alcohol 45, along with 18 mg (36%) of the diastereoisomeric alcohol 46 as colorless oils. Data for alcohol 45:1H NMR (400MHz, CDCl3) δ0.92 (m, 1H), 1.11 (m, 1H), 1.28 (m, 3H), 1.60 (m, 2H), 1.76 (m, 1H), 2.02 (m, 1H, 2-H), 2.51 and 3.59 (d of ABq, 2H, benzylic-CH2), 3.27 (m, 1H, 1-H), 7.34 (d, 2H, Ar--H), 8.15 ppm (d, 2H, Ar--H). [Compound 45 is hereinafter also referred to as COMPOUND "I" or 120154] ##STR10##

Workup

custombefore quenching with saturated aqueous NH4C1
customThe methanol was removed under diminished pressure
extractionthe resultant aqueous residue was extracted with ethyl acetate
washThe organic phase was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under diminshed pressure
customPurification by flash column chromatography (silica gel, hexanes/ethyl acetate, 4:1)

Sources & evidence

ORD record: ord-154128803df14475b33a5880f82ec9f8
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05677336

Reaction notes

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