1,2-Dimethoxyethane → HCID 67435904, compound

Participants

Reaction Conditions

Reaction Steps

{(1S,2S)-1-[(6-Bromo-naphthalen-2-ylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (210 mg, 0.5 mmol), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (336 mg, 2.0 mmol), Pd(dppf)2Cl2 (82 mg, 0.1 mmol), K3PO4 (320 mg, 1.5 mmol) was combined in the mixture of DME (2.4 mL) and water (0.6 mL). The reaction mixture was heated at 130° C. for 10 mins under Microwave condition. The reaction mixture was cooled to r.t. and was quenched by the slow addition of 1N NaOH solution (15 mL). The reaction mixture was transferred to a separatory funnel containing water (20 mL). The aqueous layer was extracted with DCM (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated. The residue was purified on silica gel (7%→17% ethyl acetate in hexanes) to afford {(1S,2S)-1-[(6-cyclopropyl-naphthalen-2-ylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (107 mg, 60% yield) as a light brown solid: LC/MS (ESI) m/e 383.3 [(M+H)+, calcd for C24H34N2O2 382.6].

Provenance & Evidence