Methyl 5-oxo-1-(propan-2-yl)pyrrolidine-3-carboxylate → 4-(Hydroxymethyl)-1-(propan-2-yl)pyrrolidin-2-one

HRID 1834807Notes

Reaction equation

HRID 1834807 reaction equation
[C:1]([CH:5]1[CH2:9][N:8]([CH:10]([CH3:12])[CH3:11])[C:7](=[O:13])[CH2:6]1)(OC)=[O:2].C(Cl)(Cl)Cl.C(O)C>C(O)C.[Ni]>[OH:2][CH2:1][CH:5]1[CH2:9][N:8]([CH:10]([CH3:11])[CH3:12])[C:7](=[O:13])[CH2:6]1

Participants

5

Reactant 2

HCID 20372066Methyl 5-oxo-1-(propan-2-yl)pyrrolidine-3-carboxylateHCID 21889567Chloroform ethanol

Product 1

HCID 213313554-(Hydroxymethyl)-1-(propan-2-yl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

92.5 g (0.5 mol) of 4-carbomethoxy-1-isopropyl-pyrrolidone in 1.2 l of ethanol were hydrogenated in the presence of about 50 g of Raney-Nickel for 48 hours at 160° - 180° C under a hydrogen pressure of 200 atmospheres. Then it was determined with the aid of thin layer chromatography (CHCl3 /C2H5OH= 95:5) if the reduction was finished. Otherwise 20 g of Raney-Nickel were added again and hydrogenated for another 24 hours. In most of the tests hydrogenation had finished after this time.

Sources & evidence

ORD record
ord-a530742c56584f4eb5ada3ddea8e102f
Source dataset
uspto-grants-1978_01
Patent number
US04071530

Reaction notes

Loading…