tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 10335872, compound

HRID 1667309Notes

Reaction equation

HRID 1667309 reaction equation
[Cl-].[CH3:2][C:3]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:30]([CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)=O>>[CH3:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:3]([CH3:2])[C:4]=1/[CH:5]=[CH:30]\[CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH2:34][CH2:33]1.[CH3:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:3]([CH3:2])[C:4]=1/[CH:5]=[CH:30]/[CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 20536643HCID 20536643, compound

Product 2

HCID 10335872HCID 10335872, compoundHCID 58870244HCID 58870244, compound

Procedure

As starting materials, 5.00 g of (2,6-dimethylbenzyl)(triphenyl)phosphonium chloride and 1.79 g of tert-butyl 4-formylpiperidine-1-carboxylate were used and treated in the same manner as in Example 1. The reaction mixture was then purified by silica gel column chromatography (hexane-ethyl acetate) to give 192 mg of tert-butyl 4-[(Z)-2-(2,6-dimethylphenyl)vinyl]piperidine-1-carboxylate (Example 2-1) and 1.96 g of tert-butyl 4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidine-1-carboxylate (Example 2-2).

Workup

  1. additiontreated in the same manner as in Example 1
  2. customThe reaction mixture was then purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-24d4fb511b90461ca670f0252a6bd047
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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