3-(Oxiran-2-ylmethoxy)pyridine → (2S)-1-Amino-3-(3-pyridinyloxy)-2-propanol

Participants

Reaction Steps

A solution of 3-(2-oxiranylmethoxy)pyridine (which was obtained in Example 123) (1.41 g) in 120 mL of saturated ammonium methanol was stirred at 0° C. for two days. The reaction mixture was concentrated to give a yellow semi-solid (1.56 g, 99.5% yield); 1H NMR (400 MHz, DMSO-d6) δ 1.60 (brs, 2 H), 2.55–2.59 (m, 1 H), 2.61–2.68 (m, 1 H), 3.67–3.72 (m, 1 H), 3.89–3.93 (m, 1 H), 4.00–4.04 (m, 1 H), 4.90 (brs, 1 H), 7.29–7.32 (m, 1 H), 7.36–7.38 (m, 1H), 8.13–8.14 (d, 1 H), 8.27 (s, 1 H); MS (ES) m/z: 138(M+); Anal. Calcd. for C7H10N2O: C, 57.13; H, 7.19; N, 16.66. Found: C, 57.83; H, 7.17; N, 18.98.

Provenance & Evidence