HCID 10591585, compound → HCID 10687113, compound

HRID 1004399Notes

Reaction equation

HRID 1004399 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH2:17])([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17])([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 10591585HCID 10591585, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10687113HCID 10687113, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-tert-butyloxycarbonyl-4-[(2-phenyl)allyl]4-hydroxypiperidine (1.67 g, 5.26 mmol) in ethyl acetate (25 ml) was hydrogenated over 1% palladium on activated carbon (0.8 g) at room temperature and 1 atm pressure of hydrogen for 1.5 hours. The mixture was filtered and the filtrate was concentrated to yield the title compound (1.47 g, 87%) as a pale yellow glass. δH (250 MHz, CDCl3) 1.27 (3 H, d, J=7), 1.36-1.60 (13 H, m), 1.73 (1 H, dd, J=15 and 4), 2.01 (1 H, dd, J=15 and 10), 2.98-3.06 (3 H, m), 3.60-3.88 (2 H, m) and 7.16-7.36 (5 H, m); m/z (ES) 320 (M+ +1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b0b536e218404713848e7d2f71c2a8f0
Source dataset
uspto-grants-2000_04
Patent number
US06048878

Reaction notes

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