2-(2,4-Dimethylcyclohex-3-en-1-yl)pyridine → HCID 69218660, compound

HRID 131088Notes

Reaction equation

HRID 131088 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C[C@@H]1C[C@H](C)CC[C@@H]1C1C=CC=CN=1>N1C=CC=CC=1>[CH3:1][C@@H:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][C@H:3]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 179724032-(2,4-Dimethylcyclohex-3-en-1-yl)pyridineHCID 692211552-[(1S,2R,4R)-2,4-Dimethylcyclohexyl]pyridine

Product 1

HCID 69218660HCID 69218660, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The relative amounts of each individual isomer is dependent on the precise conditions used for their formation and whether the hydrogenation reaction is carried out on the mixture of isomers of 2-(2,4-dimethylcyclohex-3-en-1-yl)pyridine or an individual isomer thereof. For example, it has been found that when the hydrogenation reaction is performed on 2-[(1R,2S)-2,4-dimethylcyclohex-3-en-1-yl]pyridine, the major product formed in the resulting mixture of isomers of the pyridine of the invention is 2-[(1S,2R,4R)-2,4-dimethylcyclohexyl]pyridine. By contrast, hydrogenation of 2-[(1R,2R)-2,4-dimethylcyclohex-3-en-1-yl]pyridine conveniently gives a mixture of the 2-[(1R,2R,4R)-2,4-dimethylcyclohexyl]pyridine and 2-[(1R,2R,4S)-2,4-dimethylcyclohexyl]pyridine isomers as the major reaction product.

Workup

  1. customused for their formation and whether the hydrogenation reaction
  2. customthe hydrogenation reaction

Sources & evidence

ORD record
ord-25d3c85228984d3a81359e7477bed174
Source dataset
uspto-grants-2008_06
Patent number
US07384905B2

Reaction notes

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