2-Amino-2-methyl-1-propanol → HCID 46837921, compound

Participants

Reaction Steps

Compound 4r was synthesized by a procedure similar to that described for (2S,3S)-4a using (R)-2-hydroxy-1-(naphthalen-2-yl)propan-1-one (10i, 2.5 g, 0.013 mol), Proton sponge (3.24 g, 0.0151 mol), triflic anhydride (2.4 mL, 137 mmol), and 2-amino-2-methyl-1-propanol (2.4 g, 0.027 mol) in acetonitrile (40 mL). After purification, 2.2 g (65%) of the free base 4r was isolated and converted to the hemi-D-tartrate salt: mp 179-180° C.; [α]20D −1.5° (c 0.55, CH3OH); 1H NMR (methanol-d4) δ 8.13-8.12 (m, 1H), 7.95-7.88 (m, 3H), 7.75-7.71 (m, 1H), 7.57-7.50 (m, 2H), 4.33 (s, 1H), 4.25 (d, 1H, J=11.9 Hz), 3.66-3.57 (m, 2H), 1.65 (s, 3H), 1.37 (s, 3H), 1.09 (d, 3H, J=6.6 Hz); 13C NMR (methanol-d4) δ 178.7, 139.9, 135.3, 134.6, 129.8, 129.33, 129.00, 128.0, 127.8, 127.4, 125.4, 97.4, 75.2, 67.7, 55.1, 24.5, 21.6, 14.6; LCMS (ESI) m/z 272.5 [(M-tartrate)+, M=C19H24NO5]; Anal. (C19H24NO5.0.5H2O) calcd: C, 65.88; H, 6.98; N, 4.04. found: C, 65.75; H, 7.03; N, 4.06.

Provenance & Evidence