HCID 68839471, compound → HCID 57559168, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Step 5 in a 2:1 mixture of ethanol/acetic acid (30 mL) was added palladium hydroxide on carbon powder (0.13 g, 10 wt. %). The mixture was degassed and shaken under an atmosphere of hydrogen (75 psi) at 50° C. for 12 hours. The mixture was cooled to room temperature, filtered through diatomaceous earth and the solids washed with ethanol. The filtrate was concentrated and the residue was dissolved in saturated sodium carbonate solution and extracted with chloroform (3×50 mL). The combined organic phases were dried over sodium sulfate and concentrated to afford 0.98 g (86.6%) of the product as a foam. 1H NMR (400 MHz, Methanol-d4) δ 4.49 (q, 1H), 4.20 (q, 1H), 3.86-3.67 (m, 2H), 3.61 (s, 3H), 3.28-3.21 (m, 1H), 3.19-3.09 (m, 1H), 2.96-2.87 (m, 1H), 2.74-2.64 (m, 1H), 2.63-2.47 (m, 2H), 2.38-2.23 (m, 2H). MS 278.3 (AP+, 100).

Provenance & Evidence