Ammonium Chloride → HCID 67196668, compound

Participants

Reaction Steps

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see intermediate 36) (500 mg, 1.268 mmol) and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (400 mg, 1.997 mmol) in dichloromethane (DCM) (15 ml) was stirred 45 min at room temperature under nitrogen before being treated portionwise with sodium triacetoxyborohydride (457 mg, 2.155 mmol). The resulting mixture was stirred at room temperature for 20 h then treated with a saturated NH4Cl aqueous solution (8 mL) and diluted with water (10 mL). The layers were separated and the aqueous phase was washed with DCM (2×10 mL). The combined organic layers were dried over Na2SO4 then concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 1 to 10% MeOH in DCM) gave 1,1-dimethylethyl 4-[({4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}methyl)amino]-1-piperidinecarboxylate (608 mg, 0.998 mmol, 79%) as a cream solid.

Provenance & Evidence