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

HRID 1295795Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:6]1)=O.[BH4-].[Na+].[NH4+].[Cl-].CC(C)=O>CCO>[OH:2][CH2:3][CH:5]1[CH2:6][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:8](=[O:10])[CH2:9]1

Participants

Conditions

Temperature: 12 °C

Procedure

In a 250 ml three necked flask fitted with a magnetic stirrer and reflux condenser, under inert atmosphere, a solution of 8.48 g (32 mmol, 1 eq) of 1-(4-methoxy-benzyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester al in 120 ml of EtOH is cooled down to 0° C. Solid NaBH4 (3.6 g, 96 mol, 3 eq) is then added by portions over 1.5 h, all the while maintaining the temperature between 2 and 4° C. After 2 h, the temperature is raised to 12° C. for 1 h, and lowered again to 2–4° C. A saturated solution of NH4Cl (240 ml) is added dropwise over 1 h, followed by 120 ml of acetone, and the mixture is left overnight at room temperature. The mixture is extracted by CH2Cl2 (3 times), dried on MgSO4, filtered and concentrated in vacuo to afford the crude alcohol which is purified by chromatography on silicagel (CH2Cl2/MeOH: 95/05 (v/v)) to give the pure alcohol a2 (4.3 g, 57%).

Workup

temperaturereflux condenser
temperatureall the while maintaining the temperature between 2 and 4° C
customlowered again to 2–4° C
waitthe mixture is left overnight at room temperature
extractionThe mixture is extracted by CH2Cl2 (3 times)
customdried on MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford the crude alcohol which
customis purified by chromatography on silicagel (CH2Cl2/MeOH: 95/05 (v/v))

Sources & evidence

ORD record: ord-57208d3009e942d28be00b54a7fbf6ce
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244747B2

Reaction notes

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