tert-Butyl acrylate → HCID 19989926, compound

HRID 1110848Notes

Reaction equation

HRID 1110848 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[CH:12]=[CH2:13].C([O-])(=O)C=C.[BH4-].[Na+]>[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Co](Cl)Cl>[NH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:12]([CH3:13])[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 15458tert-Butyl acrylateHCID 25188AcrylateHCID 27914Benzeneacetonitrile, 4-bromo-HCID 4311764Sodium borohydride

Product 1

HCID 19989926HCID 19989926, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24288Cobalt(II) chlorideCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

p-Bromophenylacetonitrile is first condensed with t-butyl acrylate under conditions of the palladium acetate catalyzed Heck reaction. The resulting acrylate is hydrogenated with palladium on charcoal catalyst followed by reduction (of the cyano group) with sodium borohydride in the presence of cobalt(II) chloride to yield t-butyl p-(2-aminoethyl)-phenylpropionate.

Sources & evidence

ORD record
ord-46f5f5ef186f4f01887a54452d647971
Source dataset
uspto-grants-1990_12
Patent number
US04977144

Reaction notes

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