Dicyclohexylamine → Methyl 2-(5-(cyanomethyl)-2-methoxybenzyl)-3-oxobutanoate

HRID 1617236Notes

Reaction equation

HRID 1617236 reaction equation
CN(C)C(=O)C.Br[C:8]1[CH:9]=[C:10]([CH2:16][C:17]#[N:18])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[OH:19][CH:20]([CH3:27])[C:21](=[CH2:26])[C:22]([O:24][CH3:25])=[O:23].C1(NC2CCCCC2)CCCCC1>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[C:17]([CH2:16][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([CH:9]=1)[CH2:26][CH:21]([C:20](=[O:19])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])#[N:18]

Participants

7

Reactant 4

HCID 7582DicyclohexylamineHCID 31374DimethylacetamideHCID 5226553-Bromo-4-methoxyphenylacetonitrileHCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

Product 1

HCID 68414744Methyl 2-(5-(cyanomethyl)-2-methoxybenzyl)-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 16212273Tetrabutylammonium chloride hydrateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N,N-dimethylacetamide (200 mL) was added to Pd-118 (1.009 g) and tetrabutylammonium chloride hydrate (0.916 g), followed by 2-(3-bromo-4-methoxyphenyl)acetonitrile (7 g). Methyl 3-hydroxy-2-methylenebutyrate (5.64 mL) and dicyclohexylamine (9.25 mL) were added and the solution was heated at 80° C. for 3 days. The reaction mixture was diluted with EtOAc (200 mL) and extracted with water. The organic phase was dried, filtered and evaporated under reduced pressure. The crude product was purified by chromatography to afford the subtitle compound as an orange oil, 5.01 g.

Workup

  1. extractionextracted with water
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-045612187fa44b3a8d8ec030fe56ede0
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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