Sodium borohydride → HCID 22712501, compound

HRID 458979Notes

Reaction equation

[O:1]=[C:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=1)[CH2:3][CH2:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1.[BH4-].[Na+]>>[OH:1][CH:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=1)[CH2:3][CH2:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 22712429HCID 22712429, compound

Product 1

HCID 22712501HCID 22712501, compoundYield 71.8%

Procedure

Analogous to the procedure described for Example 1A, Step B, 5-[3-oxo-4-(3-phenoxy-phenyl)-butyl]-pyrrolidin-2-one (923.6 mg, 2.86 mmol) was reduced with NaBH4 (54 mg, 1.4 mmol). Purification by medium pressure chromatography (1:1 hexanes:EtOAc to 2% MeOH in CH2Cl2 to 4% MeQOH in CH2Cl2 to 10%/MeOH in CH2Cl2) provided 5-[3-hydroxy-4-(3-phenoxy-phenyl)-butyl]-pyrrolidin-2-one (668.3 mg). 1H NMR (CDCl3) δ7.31 (m, 2H), 7.23 (m, 1H), 7.08 (m, 1H), 6.97 (d, 2H), 6.91 (d, 1H), 6.84 (m, 2H), 3.80 (m, 1H), 3.73 (m, 1H), 2.77–2.03 (m, 2H), 2.40 (m, 2H), 2.24 (m, 1H), 1.75–1.41 (m, 5H); MS 326.3 (M+1).

Workup

customPurification by medium pressure chromatography (1:1 hexanes:EtOAc to 2% MeOH in CH2Cl2 to 4% MeQOH in CH2Cl2 to 10%/MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-d1bd813bff8646b29ead3b7408547937
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192979B2

Reaction notes

Loading…