Water → 4-(Hydroxymethyl)-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-one

HRID 1374181Notes

Reaction equation

HRID 1374181 reaction equation
[BH4-].[Na+].C[O:4][C:5]([CH:7]1[CH2:11][C:10](=[O:12])[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:8]1)=O.O>C(O)C>[OH:4][CH2:5][CH:7]1[CH2:8][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:10](=[O:12])[CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 4093874Methyl 1-(4-methoxybenzyl)-5-oxopyrrolidine-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 134225594-(Hydroxymethyl)-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (15 g, 0.081 mol) was added in portions to ester 79 in ethanol (600 mL) at room temperature. After 4.5 hours water (˜200 mL) was carefully added to the reaction and the solution stirred at room temperature overnight. The resultant solid was removed by filtration and the filtrate concentrated to give alcohol 80 as an oil. 15.33 g, 81%. MS, m/z (relative intensity): 235 [M+H, 100%].

Workup

  1. customThe resultant solid was removed by filtration
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ad128edef9b640229197f5586d71e72c
Source dataset
uspto-grants-2007_01
Patent number
US07164034B2

Reaction notes

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