Benzoyl chloride → 2-Thioureidomethyl-piperidine-1-carboxylic acid tert butyl ester

反応式

C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[Na+].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][NH2:28])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CC(C)=O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][NH:28][C:11]([NH2:12])=[S:10])=[O:20])([CH3:17])([CH3:16])[CH3:15]

参加物

実験手順

Benzoyl chloride (1.2 ml) was added dropwise to sodium thiocyanate (0.90 g) in acetone (50 ml). When the addition was complete the mixture was refluxed for 15 minutes, cooled to room temperature and (RS) 2-aminomethyl-piperidine-1-carboxylic acid tert butyl ester (2.0 g) in acetone (5 ml) added. The mixture was refluxed for 2 hours, cooled to room temperature and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant) to give the title product (1.95 g).