Benzylamine → HCID 66549316, compound

Participants

Reaction Steps

To (3aR,5S,6S,7R,7aR)-2-(ethylamino)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-5-carbaldehyde (76.00 mg; 0.31 mmol; 1.00 eq.) in methanol (1.00 ml) was added benzylamine (0.05 ml; 0.46 mmol; 1.50 eq.), and sodium cyanoborohydride (9.70 mg; 0.15 mmol; 0.50 eq.) in 0.5 mL MeOH. The reaction was stirred at room temperature for 2 h. The desired product was isolated by prep HPLC (0% B for 10 min, then 0 to 30% B over 10 min, 0.1% TFA, 220 nm) to afford (3aR,5R,6S,7R,7aR)-5-[(benzylamino)methyl]-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (12.2 mg, 12%) as a white solid (once lyophilized).

Provenance & Evidence