2-Amino-2-methyl-1-propanol → HCID 46837650, compound

Participants

Reaction Steps

Compound 4e was synthesized by a procedure similar to that described for (2S,3S)-4a using (R)-1-(3-methylphenyl)-2-hydroxypropan-1-one (10e, 4.2 g, 0.026 mol), Proton sponge (6.5 g, 0.030 mol), triflic anhydride (4.60 mL, 282 mmol), and 2-amino-2-methyl-1-propanol (5.0 g, 0.056 mol) in acetonitrile (55 mL). After purification, 4.0 g (66%) of the free base 4e was isolated and converted to 3.6 g of the hemi-D-tartrate salt, which had 94% ee: mp 104-105° C.; [α]20D +11.9° (c 0.85, CH3OH); 1H NMR (methanol-d4) δ 7.43-7.38 (m, 2H), 7.28 (t, 1H, J=7.8 Hz), 7.21-7.18 (m, 1H), 4.33 (s, 1H), 4.20 (d, 1H, J=12.0 Hz), 3.52-3.45 (m, 2H), 2.38 (s, 3H), 1.61 (s, 3H), 1.36 (s, 3H), 1.06 (d, 3H, J=6.6 Hz); 13C NMR (methanol-d4) δ 179.0, 142.3, 139.4, 130.9, 129.5, 128.4, 125.0, 97.2, 75.3, 67.4, 55.2, 24.2, 21.9, 21.4, 14.4; LCMS (ESI) m/z 236.2 [(M-tartrate)+, M=C16H24NO5]; Anal. (C16H24NO5.0.75H2O) calcd: C, 59.33; H, 7.94; N, 4.32. found: C, 59.20; H, 7.88; N, 4.34.

Provenance & Evidence