(5S,6S)-6-Cyclohexylmethyl-3-isopropylidene-5-hydroxypiperidine-2-one → (3S,5S,6S)-6-Cyclohexyl-5-hydroxy-3-isopropyl-piperidin-2-one

HRID 5557Notes

Reaction equation

HRID 5557 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]1

Participants

4

Reactant 1

HCID 14991453(5S,6S)-6-Cyclohexylmethyl-3-isopropylidene-5-hydroxypiperidine-2-one

Product 1

HCID 57142969(3S,5S,6S)-6-Cyclohexyl-5-hydroxy-3-isopropyl-piperidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated to a white foamy solid which
  3. customwas taken on without further purification
  4. custom[α]D =-95.1° (c=1.075, CHCl3)

Sources & evidence

ORD record
ord-86be50e43ce8445287687f9a0c4a1bac
Source dataset
uspto-grants-1993_09
Patent number
US05244910

Reaction notes

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