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

HRID 458962Notes

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-747a1f4be3dc43cc9e37ff9423670f1e
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192979B2

Reaction notes

Loading…