Water → 1,1-Dimethylethyl 4-hydroxy-4-(2-thiazolyl)-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

2-Bromo-thiazole (0.27 mL, 2.99 mmol) was dissolved in Et2O (8 mL) and cooled down to −78° C. BuLi (1.3 mL, 2.5 M) was added dropwise. The resulting yellow solution was stirred at −78° C. for 45 min. 4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (720 mg, 3.61 mmol) in Et2O (5 mL) was then added dropwise. The reaction temperature rose to rt naturally overnight. H2O (10 mL) was added to quench the reaction and extracted with ethyl acetate. The combined organic layer was dried (MgSO4), filtered and concentrated. The residue was purified on silica gel column eluting with 33% to 50% ethyl acetate/hexanes to give 4-Hydroxy-4-thiazol-2-yl-piperidine-1-carboxylic acid tert-butyl ester (800 mg) as a colorless oil.

Provenance & Evidence