(S)-Glycidyl Trityl Ether → 2,2-Dimethyl-propionic acid (3S,4S)-1-((S)-2-hydroxy-3-trityloxy-propyl)-3-methyl-piperidin-4-yl ester
Reaction equation
[C:1]([O:20][CH2:21][C@@H:22]1[CH2:24][O:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][C@@H:26]1[C@@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30][CH2:29][NH:28][CH2:27]1>C(O)C>[OH:23][C@H:22]([CH2:21][O:20][C:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:24][N:28]1[CH2:29][CH2:30][C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:36])([CH3:35])[CH3:37])[C@@H:26]([CH3:25])[CH2:27]1Participants
4
Procedure
(S)-2-Trityloxymethyl-oxirane (636 mg, 2 mmol) and 2,2-dimethyl-propionic acid (3S,4S)-3-methyl-piperidin-4-yl ester (17, 400 mg, 2 mmol) are dissolved in 7 ml of ethanol and stirred at room temperature for 23 h. The white suspension is heated to 40° C. and stirred for additional 2 h. The reaction mixture is evaporated under reduced pressure and the crude product is purified by Flash-chromatography. (silica gel, 20% ethyl acetate in cyclohexane).