Sodium Hydroxide → 2-{1-[(Tert-butoxy)carbonyl]-4-hydroxypiperidin-4-yl}acetic acid

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Reaction Steps

A 2.0 M solution of sodium hydroxide in water (28 mL) was added to a solution of A1 (11.31 g) in methanol (40 mL). The reaction mixture was stirred for 1 h at RT. The organic solvent was removed under a vacuum and the remaining aqueous reaction mixture was repeatedly extracted with ether. The aqueous phase was acidified with 2.0 M hydrochloric acid solution in water and repeatedly extracted with DCM. The combined DCM organic phases were washed with sat. aq. NaCl solution, dried over Na2SO4 and the solvent was removed under a vacuum. 7.9 g of the desired product 4-carboxymethyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (A2) were obtained and further reacted without purification.

Provenance & Evidence