Diiodomethane → HCID 11515504, compound

Participants

Reaction Conditions

Reaction Steps

Diethylzinc (0.064 g, 0.526 mmol) was added to a flask containing CH2Cl2 (2 mL) at 0° C. A solution of TFA (0.052 ml, 0.526 mmol) in CH2Cl2 (1 ml) was slowly added to the flask containing diethylzinc over 20 min. A solution of CH2I2 (0.042 mL, 0.526 mmol) in CH2CH2 (1 mL) was added next over 20 min. followed by addition of 2-[benzyl(3-chloro-4-fluorophenyl)amino]pent-4-en-1-ol (7-5, 0.028 g, 0.088 mmol) in CH2Cl2 (1 mL). The resulting solution was warmed to 25° C. The reaction mixture was diluted with NaHCO3 (sat. aq) and extracted with CH2Cl2 (3×5 ml). The combined organic layers were dried with NaSO4, filtered, and concentrated. The crude residue was purified by reverse phase liquid chromotography (Semi Prep YMC C-18 Reverse Phase Column 5% CH3CN/H2O to 95% CH3CN/H2O with 0.1% TFA present) to yield 2-[benzyl(3-chloro-4-fluorophenyl)amino]-3-cyclopropylpropan-1-ol (9-2). MS 334.2 found 334.8 (M+H+) required.

Provenance & Evidence