1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1,1-Dimethylethyl (2R)-2-[(4-hydroxy-1-piperidinyl)carbonyl]-1-pyrrolidinecarboxylate

Participants

Reaction Steps

A mixture of (R)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2 g, 9.3 mmol), EDAC (3.5 g, 16 mmol), HOBt (1.4 g, 18 mmol), TEA (2.5 mL) and piperidin-4-ol (1.8 g, 16 mmol) in DMF (20 mL) was stirred at rt for 20 hours. The reaction was diluted with water and sodium bicarbonate, extracted with 5% methanol in DCM. The DCM was concentrated and purified on a silica gel column to give 2.6 g of (R)-2-(4-hydroxy-piperidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence