Boron trifluoride etherate → HCID 59799035, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen dissolve 7-acetyl-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.0 g, 3.32 mmol) in anhydrous THF (100 mL). Cool the solution to 0° C., add boron trifluoride diethyl etherate (3.4 mL, 26.6 mmol) and sodium cyanoborohydride (836 mg, 13.3 mmol). Remove the ice bath and stir for 5 h at RT. Dilute with EtOAc and wash with 0.1 N HCl. Separate the organic layer, dry (sodium sulfate) and concentrate. MS (ES): m/z=302 [M−H]. Mix the residue with trifluoroacetic acid (40 mL) and anhydrous DCM (50 mL) under nitrogen. Cool to 0° C. in an ice bath and add triethylsilane (3.5 mL, 21.9 mmol). After 15 min, remove the ice bath and stir at RT for 16 h. Concentrate and purify (silica gel chromatography, eluting with 10:90 EtOAc:hexanes to give the title compound (698 mg, 73%).

Provenance & Evidence