Hydrochloric Acid → HCID 86601016, compound

Participants

Reaction Steps

To a solution [(4-benzyloxy-benzenesulfonyl)-(4-oxo-pentyl)-amino]-acetic acid tert-butyl ester (compound of formula XVII, 25 g, 56 mmol) in 200 ml of tetrahydrofuran was added potassium tert-butoxide (24 ml of a 1M solution in tetrahydrofuran, 24 mmol). After stirring for about 24 hours at a temperature of about 20° C. to about 25° C., the mixture was diluted with water, acidified with 1M hydrochloric acid and extracted 3 times into ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The stereoisomers were separated by preparative HPLC on a Chiralpak AD column® eluting with 2-propanol-hexane, affording approximately 4 g of each stereoisomer of 1-[4-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid tert-butyl ester (compound of formula XVIII) as a colorless oil.

Provenance & Evidence