[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]([C:11]#[N:12])[CH2:6]1)=[O:4].C(Cl)C1C=CC=CC=1>CO.C([O-])(O)=O.[Na+].[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]([CH2:11][NH2:12])[CH2:6]1)=[O:4]
To a stirred solution of (1SR,3SR,4RS)-3-cyano-4-hydroxy-cyclopentanecarboxylic acid methyl ester (185 mg) at r.t. in methanol (5 ml) under an argon atmosphere were added benzyl chloride (0.38 ml) and 10% Pd/C (50 mg). The mixture was stirred at r.t. under a hydrogen atmosphere (balloon) overnight. The catalyst was filtered off and washed with methanol. The filtrate was concentrated to leave a brown viscous oil. This was taken up in 10 ml sat. aq. NaHCO3 and extracted with CH2Cl2/MeOH 9:1 (3×10 ml) and CH2Cl2/MeOH 4:1 (10 ml). A white solid started to precipitate out of the biphasic mixture which was filtered off. The filtrate was neutralized by the addition of 1 N HCl and concentrated to leave crude (1SR,3SR,4RS)-3-aminomethyl-4-hydroxy-cyclopentane-carboxylic acid methyl ester as a light brown solid (189 mg).
Wird geladen…
