4-Bromoanisole → HCID 68974277, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromoanisole (5.00 g, 26.70 mmol) in THF (100 mL) at −78° C. was added n-BuLi (1.9M in hexanes, 14 mL, 26.7 mmol). After the solution was stirred at −78° C. for 45 minutes, TMEDA (4.03 mL, 26.7 mmol) was added followed by a solution of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (4.76 g, 22.3 mmol) in THF (20 mL), and the mixture was stirred at −78° C. for 1 hour. The reaction was quenched with saturated aqueous NH4Cl and after work-up and purification gave 4-[hydroxy-(4-methoxy-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (3.40 g, 47%) as a white foam.

Provenance & Evidence