(5S,6S)-6-Cyclohexylmethyl-3-isopropylidene-5-hydroxypiperidine-2-one → HCID 19751082, compound

HRID 1743066Notes

Reaction equation

HRID 1743066 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][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH:1]1([CH2:7][CH:8]2[NH:13][C:12](=[O:14])[CH:11]([CH:15]([CH3:16])[CH3:17])[CH2:10][CH:9]2[OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 14991453(5S,6S)-6-Cyclohexylmethyl-3-isopropylidene-5-hydroxypiperidine-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 19751082HCID 19751082, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 5 (24.7 g, 98.4 retool) in 500 mL of ethyl acetate was treated with 2.5 g of dry palladium on carbon and hydrogenated at 4 atmospheres of hydrogen for 4 hours at ambient temperature. The reaction mixture was filtered and concentrated to a white foamy solid which was taken on without further purification. m.p. 97°-99° C. [α]D =-95.1° (c=1.075, CHCl3). IR (KBr) 3605, 3400, 2925, 1642 cm-1. 1H NMR (300 MHz, CDCl3) δ6.3 (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, 3H). 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. customm.p. 97°-99° C. [α]D =-95.1° (c=1.075, CHCl3)

Sources & evidence

ORD record
ord-617a7c7e9db645ac995a24ee8239dc3c
Source dataset
uspto-grants-1994_08
Patent number
US05342981

Reaction notes

Loading…