HCID 68521328, compound → HCID 57850280, compound

HRID 445085Notes

Reaction equation

HRID 445085 reaction equation
[CH2:1]([O:3][C:4](/[CH:6]=[C:7]1/[C:8]([CH3:21])([CH3:20])[CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]/1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:8]1([CH3:20])[CH3:21])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 68521328HCID 68521328, compound

Product 1

HCID 57850280HCID 57850280, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (E)-tert-butyl 4-{(ethoxycarbonyl)methylene}-3,3-dimethylpiperidine-1-carboxylate (784 mg, 2.64 mmol) in MeOH (10 mL) containing Pd/C (131 mg) was hydrogenated at 1 atm. After 10 h, the mixture was filtered, and the filter cake was washed with MeOH. The combined filtrates were concentrated to afford the titled compound (540 mg, 68%): 1H NMR (CDCl3) δ 4.13 (q, J=6.8 Hz, 2H), 4.05 (m, 1H), 3.57 (m, 1H), 2.57 (m, 1H), 2.46 (dd, J=15.2, 3.2 Hz, 1H), 1.93 (dd, J=15.2, 10.4 Hz, 1H), 1.76 (m, 1H), 1.59-1.50 (m, 2H), 1.45 (s, 9H) 1.34 (m, 1H), 1.26 (t, J=6.8 Hz, 3H), 0.91 (s, 3H), 0.79 (s, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. washthe filter cake was washed with MeOH
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-fed961533b0e477f9c86e00bc4ef3e7e
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

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