Acetaldehyde → HCID 178463311, compound

Participants

Reaction Steps

To a solution of methyl 3-(((trans)-4-((tert -butoxycarbonyl)amino)cyclohexyl)amino)-5-chloro-2-methylbenzoate (330 mg, 0.831 mmol) and acetaldehyde (200 μL, 3.56 mmol) in 1,2-dichloroethane (DCE) (5 mL) was added acetic acid (400 μL) and the mixture was stirred at room temperature for 1 h. The mixture was cooled to 0° C. in an ice bath and sodium triacetoxyborohydride (700 mg, 3.30 mmol) was added (very thick suspension that slowly dissolved). The reaction was allowed to warm to room temperature and stirred overnight. LCMS showed the reaction was mostly complete. The reaction was neutralized with sat. NaHCO3, extracted with CH2Cl2, dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (Analogix, 5 to 20% EtOAc in hexanes) and the pure fractions were combined and evaporated to dryness to give the product methyl 3-(((trans)-4-((tert -butoxycarbonyl)amino)cyclohexyl)(ethyl)amino)-5-chloro-2-methylbenzoate (250 mg, 0.588 mmol, 70.8% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) 6=7.44 (d, J =2.3 Hz, 1 H), 7.38 (d, J=2.3 Hz, 1 H), 6.68 (d, J=7.8 Hz, 1 H), 3.83 (s, 3 H), 3.16 (br. s., 1 H), 3.05 (q, J=6.9 Hz, 2 H), 2.59 (t, J=11.1Hz, 1 H), 2.34 (s, 3 H), 1.82-1.64 (m, 4 H), 1.47-1.38 (m, 2 H), 1.36 (s, 9 H), 1.16-1.04 (m, 2 H), 0.78 (t, J=6.9 Hz, 3 H). MS(ES) [M+H]+ 425.2.

Provenance & Evidence