Methyl chloroformate → HCID 21077865, compound

Participants

Reaction Steps

A solution of methyl chloroformate (0.52 ml, 6.73 mmol) in dichloromethane (5 ml) was added dropwise over 0.1 h to a stirred solution of (RS)-1-(tert-butyloxycarbonyl)-2-(2-hydroxyethyl)piperazine (D6) (1.4 g, 6.09 mmol) and triethylamine (1.7 ml, 12.2 mmol) in dichloromethane (45 ml) at 0° C. under argon. The resultant mixture was stirred at room temperature for 18 h, washed with saturated sodium hydrogen carbonate and the organic layer dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 10-100% ethyl acetate in hexane to give the title compound as a colourless gum (1.36 g, 78%). 1H NMR (CDC13)δ: 1.48 (9H, s), 1.60-1.95 (2H, m), 2.80-3.00 (2H, m), 3.05-3.45 (2H, m), 3.50-3.70 (2H, m), 3.70 (3H, s), 3.75-4.45 (4H, m).

Provenance & Evidence