3-Methyl-2-butenoic acid → HCID 18787214, compound

HRID 1107425Notes

Reaction equation

HRID 1107425 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][CH:5](O)[CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.CC(C)=CC(O)=[O:20].C1(=O)CCCC=C1.[C-:30]#[N:31].C([Al+]CC)C>O1CCCC1>[C:30]([C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3][C:2]([CH3:15])([CH3:1])[CH2:7][C:6](=[O:20])[CH2:5]1)#[N:31]

Participants

6

Reactant 4

HCID 109313-Methyl-2-butenoic acidHCID 135942-Cyclohexen-1-oneHCID 16686413Diethyl aluminum cyanideHCID 18787233HCID 18787233, compound

Product 1

HCID 18787214HCID 18787214, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The amines where R0 contains a 5,5-dimethyl-3-phenyl-2-cyclohexanol may be prepared substantially as described in Mestres et al., Tetrahedron, volume 50, page 2571 (1994). For example, in a tandem Michael-Dieckmann decarboxylative annulation of trans-βmethylcinnamic acid and 3,3-dimethylacrylic acid, the cyclohexenone was stirred with diethylaluminum cyanide in tetrahydrofuran at room temperature overnight to provide 3-cyano-5,5-dimethyl-3-phenylcyclohexanone which was then hydrogenated over 5% rhodium on alumina to give the corresponding amine.

Workup

  1. custommay be prepared substantially

Sources & evidence

ORD record
ord-19d51c06a6de459bb5c6ad04c4994966
Source dataset
uspto-grants-2000_05
Patent number
US06060484

Reaction notes

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