2-[(2S,3S)-2-methyl-1-[(1S)-1-phenylethyl]pyrrolidin-3-yl]propan-2-ol → (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine
Reaction equation
[CH3:1][C@H:2]1[C@@H:6]([C:7]([OH:10])([CH3:9])[CH3:8])[CH2:5][CH2:4][N:3]1[C@H](C1C=CC=CC=1)C>[C].[Pd].CO>[OH:10][C:7]([C@H:6]1[CH2:5][CH2:4][NH:3][C@H:2]1[CH3:1])([CH3:9])[CH3:8]Participants
4
Procedure
A mixture of 2-[(2S,3S)-2-methyl-1-[(1S)-1-phenylethyl]pyrrolidin-3-yl]propan-2-ol (2.00 g) synthesized by a known method, 10% palladium-carbon (50% water-containing product, 172 mg) and methanol (30 ml) was stirred under a hydrogen atmosphere at room temperature for 60 hr. The catalyst was removed by filtration through celite, and the mother liquor was concentrated. The obtained oily substance was dissolved in methanol, oxalic acid dihydrate (510 mg) was added thereto, and the mixture was concentrated. The residue was crystallized from diethyl ether to give the title compound (1.47 g, 1/2 hydrate).