Tert-butyl 3-aminoazetidine-1-carboxylate → HCID 86727434, compound

Participants

Reaction Steps

A mixture of 6-amino-4-methyl-7-phenoxy-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.090 g, crude from previous step), tert-butyl 3-aminoazetidine-1-carboxylate (0.087 g, 0.51 mmol) and sodium cyanoborohydride (0.00032 g, 0.51 mmol) in MeOH (2.7 mL) and AcOH (0.3 mL) was heated at reflux overnight. The reaction mixture was cooled to ambient temperature and diluted with MeOH (10 mL). The solution was purified by preparative HPLC (Table 3, Method 3) to give 3-(4-methyl-3-oxo-7-phenoxy-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.015 g, 12% over 2 steps) as a colorless oil. LC/MS (Table 1, Method 2) Rt=1.188 min; MS m/z: 502 [M+23]+

Provenance & Evidence