Triethylamine → 4-Piperidinemethanol, 1-benzoyl-

Participants

Reaction Conditions

Reaction Steps

To a solution of 2 g of 1-benzoyl-isonipecotic acid (step A) in 50 mL THF at 0° C. were added 1.47 g of triethylamine and 1.99 g of isobutyl chloroformate. The reaction was stirred for 1 hr at 0° C. To a solution of 1.10 g of sodium borohydride in 30 ml DMF at 0° C. was slowly added the above THF mixture. The reaction was again stirred for 1 hr at 0° C. Water (80 mL) was slowly added to the reaction and the mixture was extracted with 5×80 mL of EtOAc and the combined organic layers were dried over MgSO4. The solvent was then evaporated under reduced pressure. The residue was purified by flash chromatography with 1:1 hexane EtOAc followed by hexane:EtOAc:MeOH, 50:50:5 to give 1.865 g of the title compound. ESI-MS 219.9 (M+H); HPLC A: 2.34 min.

Provenance & Evidence