Methylamine → HCID 53810243, compound

Participants

Reaction Steps

To a solution of the aldehyde of Example 198, Step A (340 mg, 1 mmol) in dry DME (10 mL) was added about 250 mg MgSO4 followed by methyl amine (1 mL of a 2.0M solution in MeOH, 2 equiv). The reaction was monitored by MS for the consumption of aldehyde and formation of the corresponding imine (+APcl(M+1)+ 354). Once imine formation was complete, NaOAc (820 mg, 10 mmol) and NaCNBH3 (248 mg, 4 mmol) were added and the mixture was stirred at room temperature for 1 h. The mixture was filtered through Celite® and the filtrate was concentrated. The resulting residue was taken up in EtOAc (25 mL) and washed with 1N NaOH and brine solutions, respectively. The organic phase was dried over MgSO4 and concentrated to deliver the crude amine (360 mg). Purification by flash chromatography (SiO2 gel, 3:1:0.2. EtOAc:Hexane:EtOH) delivered 210 mg (59%) of the diamine of Example 198, Step B: +APcl MS (M+1)+ 356, (M−tBu+1)+ 300, (M−Boc+1)+ 256; 1H NMR=400 MHz (CDCl3) δ: 7.21 (m, 1H), 6.81 (m, 2H), 2.51 (br s, 3 H), 1.42 (s, 9H).

Provenance & Evidence