Sodium triacetoxyborohydride → HCID 59444140, compound

Participants

Reaction Conditions

Reaction Steps

1-[4-(Ethyloxy)-1-methylcyclohexyl]-4-piperidinone (D8) (0.350 g, 1.462 mmol)+ethyl (2E)-3-(2-amino-4-methylphenyl)-2-propenoate (D142) (0.1 g, 0.487 mmol) were placed in a microwave vial with 1,2-dichloroethane (DCE) (0.974 mL) and stirred for 10 mins. Sodium triacetoxyborohydride (0.387 g, 1.827 mmol) was added and the mixture heated at 140° C. for 10 mins. LCMS of the crude reaction mixture showed product (67% by u.v.). The reaction was quenched with NaHCO3 (10 mL, sat. aq) and then extracted with DCM (3×20 mL). The organic phases were combined, dried (phase sep. cartridge) and passed through a SCX-3 cartridge, eluting with DCM/MeOH to remove any neutral/acidic by-products. The product was eluted from the cartridge with 0.5 M NH3/MeOH to give a dark yellow oil. The crude product was purified by column chromatography using a 5 g cartridge and eluting with DCM-8% NH3/MeOH/DCM to give the product as a bright yellow/green oil (0.117 g, 56%).

Provenance & Evidence