Methanol → Methylamine

Participants

Reaction Steps

N-(4-(3,5-bis(trifluoromethyl)benzyloxy)-3-hydroxy-3-phenylbutyl)-2,2,2-trifluoro-N-methylacetamide (7.5 mg, 0.015 mmol) was dissolved in excess ammonia in methanol (2 M, 2 ml) and stirred at room temperature for 1 hour. The solution was concentrated, and the residue was purified by preparative HPLC and to give mono-methyl amine as a TFA salt. 1H NMR (500 MHz, MeOH) δ ppm 7.69 (s, 2H) 7.68 (s, 1H) 7.31–7.38 (m, 2 H) 7.19–7.25 (m, 2 H) 7.14 (t, J=6.71 Hz, 1 H) 4.49–4.56 (m, 2 H) 3.60–3.64 (m, 1 H) 3.53–3.57 (m, 1 H) 2.77–2.84 (m, 1 H) 2.66–2.74 (m, 1 H) 2.42–2.47 (m, 3 H) 2.16–2.24 (m, 1 H) 2.06 (ddd, J=13.89, 7.93, 5.65 Hz, 1 H); 13C NMR (126 MHz, MeOH) δ ppm 144.34 (s) 143.23 (s) 132.78 (q, JCCF=33.94 Hz) 129.56 (s) 128.83 (s) 128.61 (s) 126.65 (s) 124.90 (q, JCF=271.28 Hz) 122.31 (s) 79.55 (s) 77.00 (s) 72.87 (s) 46.94 (s) 35.46 (s) 33.81 (s); HRMS [ESI, MH+] m/z calcd for C20H22NO2F6 422.1555, found 422.1552.

Provenance & Evidence