HCID 13341009, compound → 2-Pyrrolidinone, 3-hydroxy-1-(3-hydroxy-4-methoxybenzoyl)-, (R)-

Reaction equation

C([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:12]([N:14]1[CH2:18][CH2:17][C@@H:16]([OH:19])[C:15]1=[O:20])=[O:13])C1C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:12]([N:14]1[CH2:18][CH2:17][C@@H:16]([OH:19])[C:15]1=[O:20])=[O:13]

Participants

Procedure

2.20 g of (R)-1-(3-benzyloxy-4-methoxybenzoyl)-3-hydroxy-2-pyrrolidinone are hydrogenated in 60 ml of tetrahydrofuran over 1.80 g of 5% palladium/carbon with hydrogen at atmospheric pressure. After removal of the catalyst by filtration, concentration of the filtrate and recrystallization of the residue from ethyl acetate/n-hexane, there is obtained (R)-1-(3-hydroxy-4-methoxybenzoyl)-3-hydroxy-2-pyrrolidinone of melting point 129°-131°; [α]D20 =+175°; [α]54620 =+216°; [α]43620 =+451° (chloroform, c=1.0).