Methane → HCID 12914604, compound

Participants

Reaction Steps

A solution of 5-amino-1-pentanol (0.650 g, 6.31 mmol) in methanol (15 ml) was cooled to 0° C. and treated with triethylamine (1.62 ml, 11.6 mmol) followed by acetic anhydride (0.891 ml, 9.45 mmol). The reaction mixture was stirred at room temperature overnight. TLC analysis (8% methanol/dichloromethane) then revealed some unreacted material, so additional triethylamine (1.6 ml, 11.6 mmol) and acetic anhydride (0.9 ml, 9.5 mmol) were added at room temperature and the solution was stirred 16 h further. Concentration in vacuo and flash chromatography (7% methanol/dichloromethane) afforded III-20 (1 g, 94% yield) as a pale yellow oil: IR (film) 3300 (s), 3100 (m), 2940 (s), 2870 (m), 1650 (s), 1560 (s), 1439 (m), 1372 (m), 1295 (m), 1220 (w), 1180 (w), 1050 (m), 1010 (w) cm-1 ; 1H NMR (500 MHz, CDCl3) δ6.21 (s, 1 H), 3.62 (t, J=6.4 Hz, 2 H), 3.23 (dd, J=12.9, 7.0 Hz, 2 H), 2.87 (s, 1 H), 1.97 (s, 3 H), 1.60-1.50 (m, 4 H), 1.43-1.37 (m, 2 H); high resolution mass spectrum (Cl, CH4) m/z 146.1164 [(M+H)+ ; calcd for C7H16NO2 : 146.1181].

Provenance & Evidence