Sodium borohydride → HCID 22712501, compound

HRID 2219691Notes

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 Compound 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% MeOH 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) δ 7.31 (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% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-5b36d6b6b94743a58929d4cd34167c04
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414071B2

Reaction notes

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