N-Methyl dicyclohexylamine → HCID 57551724, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the product from step i) (170 mg), tetrabutylammonium chloride (10 mg), Pd-118 (24 mg) and N-methyldicyclohexylamine (0.12 mL) in N,N-dimethylacetamide (3 mL) was evacuated and flushed with nitrogen (×3) before the addition of allyl alcohol (0.05 mL). The resultant solution was stirred under nitrogen at 70° C. for 2 hours. The reaction mixture was cooled to room temperature and dilute hydrochloric acid (1N, 2 mL) was added, followed by dichloromethane (10 mL). The resulting suspension was filtered and the filtrate was washed with water (2×5 mL). The organic phase was separated and treated with dimethylamine hydrochloride (0.181 g) followed by sodium triacetoxyborohydride (0.157 g). The mixture was then stirred at room temperature for 30 minutes. The reaction mixture was filtered and poured directly onto a silica column (10 g) (eluting with 3% methanol in dichloromethane) to afford the sub-titled compound (0.12 g).

Provenance & Evidence