Sodium borohydride → 5-(3-Hydroxy4-phenyl-butyl)-pyrrolidin-2-one

HRID 352573Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(3-oxo-4-phenyl-butyl)-pyrrolidin-2-one (5.902 g, 25.52 mmol) in EtOH (30 mL) at 0° C. was added NaBH4 (485 mg, 12.76 mmol) and the reaction mixture was stirred at 0° C. for 2.5 h. The reaction mixture was quenched with saturated aqueous ammonium chloride. Water and CH2Cl2 were added. The aqueous layer was washed with CH2Cl2 (2×) and the combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2) to yield 4.3 g of 5-(3-hydroxy-4-phenyl-butyl)-pyrrolidin-2-one. 1H NMR (CDCl3) δ7.35-7.16 (m, 5H), 6.02 (m, 1H), 3.80 (m, 1H), 3.63 (m, 1H), 2.79 (m, 1H), 2.64 (m, 1H), 2.26 m, 3H), 1.72-1.22 (m, 6H).

Workup

customThe reaction mixture was quenched with saturated aqueous ammonium chloride
additionWater and CH2Cl2 were added
washThe aqueous layer was washed with CH2Cl2 (2×)
dry with materialthe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by medium pressure chromatography with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-3ef5d39fdb46413aaf9c080b8e0cdf0e
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747054B2

Reaction notes

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