(5S,6S)-6-Cyclohexylmethyl-3-isopropylidene-5-hydroxypiperidine-2-one → (3S,5S,6S)-6-Cyclohexyl-5-hydroxy-3-isopropyl-piperidin-2-one
Reaction equation
[CH:1]1([CH2:7][C@@H:8]2[NH:13][C:12](=[O:14])[C:11](=[C:15]([CH3:17])[CH3:16])[CH2:10][C@@H:9]2[OH:18])[CH2:6][CH2:5][CH2:4][CH2:3]C1>C(OCC)(=O)C.[Pd]>[CH:7]1([C@@H:8]2[NH:13][C:12](=[O:14])[C@H:11]([CH:15]([CH3:16])[CH3:17])[CH2:10][C@@H:9]2[OH:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:1]1Participants
4
Procedure
A solution of the product of Example 80e (24.7 g, 98.4 mmol) in 500 ml of ethyl acetate was treated with 2.5 g of dry Pd/C and hydrogenated at 4 atm for 4h at ambient temperature. The reaction mixture was filtered and concentrated to a white foamy solid which was taken on without further purification. mp 97°-99° C.; [α]D =-95.1° (c=1.075, CHCl3); IR (KBr, cm-1) 3605, 3400, 2925, 1642; 1H NMR (300 MHz, CDCl3) δ 6.3 (bs, 1H), 4.11 (m, J=4.5, 1H), 3.47 (m, 1H), 2.72 (bs, 1H), 2.5 (m, 1H), 2.3 (m, 1H), 1.9 (m, 1H), 1.8-1.5 (m, 8H), 1.43-1.12 (m, 6H), 0.97 (d, 3H), 0.87 (m, 3 H); 13C NMR (75.5 Hz, CDCl3) ppm 174.2, 67.1, 52.6, 44.3, 37.7, 34.5, 33.8, 32.4, 27.6, 26.4, 26.3, 26.2, 26.0, 20.2, 17.4.