Water → Tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-hydroxypiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 1.0 M solution of lithium hexamethyldisilazide (LiHMDS) in THF (40 mL, 40 mmol) was cooled to −70° C. under a nitrogen atmosphere. EtOAc (3.91 mL, 40 mmol) was slowly added dropwise thereto. The reaction mixture was stirred for 10 min at −70° C. stirred and a solution of 1-(tert-butyloxycarbonyl)-4-piperidone (7.34 g, 36.84 mmol, Lancaster, order number: 13361) in THF (16 mL) was slowly added dropwise thereto. After heating the reaction solution to 0° C., water (50 mL) was added and the reaction mixture repeatedly extracted with ether. The combined organic phases were washed with sat. aq. NaCl solution, dried over Na2SO4 and the solvent was removed under a vacuum. 11.31 g of the desired product 4-ethoxycarbonylmethyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (A1) were obtained and further reacted without purification.

Provenance & Evidence