HCID 70160773, compound → HCID 70159678, compound

Participants

Reaction Steps

The product from Example 1E (9.7 g, 24.5 mmol) and 5% Pt/C (2.0 g) in ethanol (1 L) was hydrogenated for 16 hours at ambient temperature under 4 atm of hydrogen, filtered through Celite® and concentrated to provide a mixture of diastereomers. The diastereomers were separated by flash chromatography on silica gel with 100:1:1 diethyl ether:ethanol:triethylamine to provide the title compound as the more mobile band. Rf 0.38 (100:1:1 diethyl ether:ethanol:triethylamine); mp 91-92° C.; [α]23D −3.4° (c 1.105, CHCl3); 1H NMR (300 MHz, CDCl3) δ1.35 (d, 3H), 1.45 (bs, 1H), 2.50-2.62 (m, 2H), 3.33 (bm, 1H), 3.73 (q, 1H), 3.86 (dd, 1H), 4.15 (dd, 1H), 4.21 (bs, 1H), 6.62 (m, 2H), 6.75 (m, 2H), 7.20-7.40 (m, 5H).

Provenance & Evidence