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

HRID 1167901Notes

Reaction equation

HRID 1167901 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-8c59d00d326c49aea794095b768ba196
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

Loading…