Methanol → Methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate

HRID 382809Notes

Reaction equation

HRID 382809 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH:11]2[CH2:12][N:13]([CH3:22])[CH2:14][CH2:15]/[C:16]/2=[CH:17]\[C:18]([O:20][CH3:21])=[O:19])=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2].[H][H].[CH3:27][OH:28]>[Pd]>[C:18]([O:20][CH2:21][CH3:27])(=[O:19])[CH3:17].[CH3:8][OH:9].[NH4+:13].[OH-:28].[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C@H:11]2[C@@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]([CH3:22])[CH2:12]2)=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2].[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C@H:11]2[C@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]([CH3:22])[CH2:12]2)=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2]

Participants

7

Reactant 3

HCID 887MethanolHCID 86757543methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetateHCID 178418361HCID 178418361, compound

Product 3

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 69823052Methyl trans-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetateYield 21%HCID 69823475Methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetateYield 77%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

g 2) A solution of 11.7 g (35.3 mmol) of methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate in 100 ml of methanol was treated with 500 mg of Pd on charcoal and hydrogenated with hydrogen at room temperature for 12 hours. The catalyst was filtered off and the filtrate was evaporated. Chromatography (silica gel, ethyl acetate/methanol/NH4OH 200:10:1) yielded 9.14 g (77%) of methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.23 (silica gel ethyl acetate methanol/NH4OH 200:10:1) and 2.56 g (21%) of methyl trans-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.12 (silica gel, ethyl acetate/methanol/NH4OH 200:10:1).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-10d2d1a2c6cc448f879dc2afd98ac5e9
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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