Dimethyl Sulfoxide → 1-(Phenylmethyl)-4-piperidinepropanal

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.93 mL of oxalyl chloride in 20 mL of CH2Cl2 at −78° C. was added 1.13 mL of DMSO in 0.1 mL of CH2Cl2 dropwise. After stirring 5 min, a solution of 3-(1-benzyl-piperidin)yl)propan-1-ol (form Step C) in 8 mL of CH2Cl2 was added dropwise. After stirring 15 minutes, 0.75 mL of diisopropylethylamine was added. The reaction was warmed to 0° C. and stirred for 20 min. After quenching with H2O, the reaction was diluted with 50 mL of CH2Cl2. The aqueous layer was extracted with 2×50 mL Of CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated to give 612 mg the title compound, which was used for the next step without further purification

Provenance & Evidence