1,2-Dichloroethane → HCID 19611597, compound

Participants

Reaction Conditions

Reaction Steps

The amine hydrochloride 7 (978 mg) was partitioned between dilute aqueous NaHCO3 solution and methylene chloride. The aqueous layer was washed with three portions of CH2Cl2, and the combined organics were dried (Na2SO4), filtered, and concentrated in vacuo to provide the free amine. To a solution of the amine in 11 mL of 1,2-dichloroethane at 0° C. was added 4Å powdered molecular sieves (2 g), followed by sodium triacetoxyborohydride (3.04 g). The aldehyde 6 (1.21 g) was added, and the reaction was stirred at 0° C. After 15 hours, the reaction was poured into EtOAc, washed with saturated aqueous NaHCO3, and the aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was taken up in 60 mL of 5:1 benzene:CH2Cl2, and propylamine (10 mL) was added. The reaction was stirred for 12 hours, then concentrated in vacuo, and purified by silica gel chromatography (5% MeOH/CHCl3) to provide the titled compound 8 as a white foam.

Provenance & Evidence