Methane → HCID 40429395, compound

HRID 1976615Notes

Reaction equation

HRID 1976615 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 297MethaneHCID 887MethanolHCID 53718989HCID 53718989, compound

Product 1

HCID 40429395HCID 40429395, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-(2-methoxycarbonylvinyl)-piperidine-1-carboxylic acid t-butyl ester (1.46 g, 5.41 mmol) in 1:1 methanol:methylene chloride (40 mL) was added 10% palladized charcoal (0.129 g). The mixture was hydrogenated (59 psi) for 5.5 h. The catalyst was removed by filtration through a bed of celite and the solution concentrated in vacuo. Purification by silica gel chromatography provided the product (1.10 g, 75%).

Workup

  1. customfor 5.5 h
  2. customThe catalyst was removed by filtration through a bed of celite
  3. concentrationthe solution concentrated in vacuo
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-17563194d8084e81808eca16634317f4
Source dataset
uspto-grants-2001_05
Patent number
US06228872B1

Reaction notes

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