Imidazole → HCID 86661577, compound

Participants

Reaction Steps

To a stirred solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (400 mg, 1.98 mmol) in DMF (2 mL) was added TBDPS chloride (0.52 mL, 1.98 mmol) and imidazole (297 mg, 4.47 mmol) and the reaction stirred at RT for 16 h afterwhich time the reaction mixture was diluted with brine (10 mL), washed with CH2Cl2 (3×25 mL) and the organics combined and dried through a phase separation cartridge and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with EtOAc and increasing the polarity to 30% EtOAc/isohexane to obtain 4-(tert-butyl-diphenyl-silanyloxy)-piperidine-1-carboxylic acid tert-butyl ester as a colourless oil (545 mg, 62%).

Provenance & Evidence