Acetic Acid → HCID 66707028, compound

Participants

Reaction Steps

Dissolve 6-benzylamino-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (50 mg, 0.11 mmol) in acetonitrile (3 mL) and add a solution of formaldehyde in water (37%, 85 μL, 0.97 mmol) followed by sodium cyanoborohydride (16.5 mg, 0.26 mmol). Heat the solution to reflux 1 h, cool to ambient temperature, add glacial acetic acid (0.25 mL) and stir 72 h. Pour the mixture into water (100 mL) containing methanol (1 mL), extract with DCM (3×20 mL), wash the organic extracts with brine, dry over MgSO4, filter and concentrate in vacuo. Dissolve the resulting residue in DCM (5 mL), and add trifluoroacetic acid (2 mL). Stir for 2 h at ambient temperature and evaporate the solvent. Purify by SCX chromatography. Use a method similar to the General Procedure 2-1 to give the title compound (45 mg, 95%). MS (ES+) m/z: 301 (M+H)+.

Provenance & Evidence