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

HRID 458020

Reaction equation

HRID 458020 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-d710770dbbb94e9eb465409b61058f5b
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Linked notes

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