tert-Butyl acrylate → HCID 19989926, compound

HRID 973429Notes

Reaction equation

HRID 973429 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 conditons 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-29e1a48e3ca04ee288f8d102dae97d5e
Source dataset
uspto-grants-1991_11
Patent number
US05063233

Reaction notes

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