tert-Butyl acrylate → HCID 19989926, compound

HRID 1031509Notes

Reaction equation

HRID 1031509 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. Condensation with 2-alpha,3-alpha-dihydroxy-4β-[9-(2-chloroadenyl)]-cyclopentane-1β-N-ethylcarboxamide yields the t-butyl ester of compound (a) which is hydrolyzed to compound (a) with aqueous hydrochloric acid.

Sources & evidence

ORD record
ord-ae5f9b9bd9984ba48be9de154ea5bfd0
Source dataset
uspto-grants-1990_09
Patent number
US04954504

Reaction notes

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