Sodium borohydride → 5-[4-(3-Chloro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one

HRID 458972Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=[O:18])[CH2:10][CH2:11][CH:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:18])[CH2:10][CH2:11][CH:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 129700905-[4-(3-Chloro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

Product 1

HCID 129700915-[4-(3-Chloro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-oneYield 79.9%

Procedure

Analogous to the procedure described for Example 1A, Step B, 5-[4-(3-chloro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (1.9 g, 7.15 mmol) was reduced with NaBH4 (135 mg, 3.57 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 8% MeOH in CH2Cl2) provided 5-[4-(3-chloro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one (1.53 g). 1H NMR (CDCl3) δ7.22 (m, 3H), 7.07 (m, 1H), 6.51 (d, 1H), 3.82 (m, 1H), 3.66 (m, 1H), 2.77 (m, 1H), 2.66 (m, 1H), 2.33–2.19 (m, 3H), 2.04 (d, 1H), 1.74–1.45 (m, 5H); MS 268.2 (M+1).

Workup

customPurification by medium pressure chromatography
washeluting with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 8% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-a565c010fdc64d65b61f98f4694a03c1
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192979B2

Reaction notes

Loading…