Triethylamine → HCID 59437177, compound

Participants

Reaction Steps

A solution of triphosgene (35 mg, 0.12 mmol) in anhydrous CH2Cl2 (500 μL) was added slowly to a solution of 1-(1-adamantylmethylamino)-5-methylhexan-3-ol (100 mg, 0.36 mmol) and Et3N (50 μl, 0.257 mmol) in anhydrous CH2Cl2 (2 mL) at 0° C. The reaction mixture was stirred for 1 h. Solvent was removed and the residue was purified by preparative TLC to give 3-((1-adamantyl)methyl)-6-isobutyl-1,3-oxazinan-2-one (80 mg, 74%). 1H NMR (MeOD, 400 MHZ): δ=0.93-0.98 (q, 6H), 1.35-1.44 (m, 1H), 1.50-2.08 (m, 18H), 2.87-2.94 (d, 1H), 3.12-3.20 (d, 1H), 3.30-3.40 (m, 1H), 3.49-3.61 (m, 1H), 4.35-4.45 (m, 1H); MS m/z=306.

Provenance & Evidence