(4aR,7aR)-benzyl hexahydrocyclopenta[b][1,4]oxazine-4(4aH)-carboxylate → (4aR,7aR)-octahydrocyclopenta[b][1,4]oxazine

Participants

Reaction Steps

To (4aR,7aR)-benzyl hexahydrocyclopenta[b][1,4]oxazine-4(4aH)-carboxylate (199.5 mg, 0.76 mmol) dissolved in ethyl acetate (5 mL) was added palladium (10 weight % on carbon, 81 mg, 0.076 mmol). Added hydrogen gas via balloon, and the reaction was stirred under a hydrogen atmosphere for two hours at room temperature. The mixture was filtered over celite and concentrated under reduced pressure to afford (4aR,7aR)-octahydrocyclopenta[b][1,4]oxazine. 1H NMR (500 MHz, CDCl3) δ 3.90 (d, J=11.5, 1H), 3.64 (t, J=11.6, 1H), 3.17 (dd, J=9.2, 18.3, 1H), 2.96 (t, J=11.9, 1H), 2.88 (d, J=12.2, 1H), 2.59-2.47 (m, 1H), 1.89 (dd, J=9.1, 18.4, 1H), 1.84-1.61 (m, 4H), 1.57-1.44 (m, 1H), 1.38-1.26 (m, 1H).

Provenance & Evidence