Sodium borohydride → 5-(4-(4-Fluoro-phenyl)-3-hydroxy-butyl)-pyrrolidin-2-one

HRID 458985Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[BH4-].[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride2×

HCID 227125185-[4-(4-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

Product 1

HCID 227124475-(4-(4-Fluoro-phenyl)-3-hydroxy-butyl)-pyrrolidin-2-oneYield 75.5%

Procedure

Analogous to the procedure described for Example 1A, Step B, 5-[4-(4-fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (2.64 g, 10.6 mmol) was reduced with NaBH4 (400 mg, 10.5 mmol) at room temperature for 1 h. Additional NaBH4 (150 mg, 3.95 mmol) was added and the reaction mixture was stirred for 20 h. Purification by medium pressure chromatography using a solvent gradient (CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2) provided 5-[4-(4-fluoro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one (2.01 g). 1H NMR (CDCl3) δ7.14 (m, 2H), 6.98 (m, 2H), 6.78 (m, 1H), 3.76 (m, 1H), 3.65 (m, 1H), 2.76 (m, 1H), 2.64 (m, 1H), 2.32–2.18 (m, 4H), 1.72–1.47 (m, 5H).

Workup

customPurification by medium pressure chromatography

Sources & evidence

ORD record: ord-09b27c4598e14ad38432636324f4e9eb
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192979B2

Reaction notes

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