HCID 14213078, compound → (2R)-2-Benzyl-4-tert-butoxy-4-oxobutanoic acid

HRID 373657Notes

Reaction equation

HRID 373657 reaction equation
C([O:8][C:9](=[O:26])[C@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1>[Pd].CO>[C:15]([O:14][C:12]([CH2:11][C@@H:10]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:9]([OH:26])=[O:8])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 14213078HCID 14213078, compound

Product 1

HCID 13584974(2R)-2-Benzyl-4-tert-butoxy-4-oxobutanoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The diester from Example 98 (1.41 g) and 10% palladium on carbon (0.70 g) in methanol were stirred under a hydrogen atmosphere for 2 h. Filtration and solvent evaporation afforded 1.03 g (98%) of the desired product as an oil. 1H NMR (CDCl3, TMS) δ 7.1-7.4 (m,5H), 2.95-3.15 (m,2H), 2.72 (dd,1H), 2.56 (dd,1H), 2.32 (dd,1H), 1.40 (s,9H).

Workup

  1. filtrationFiltration and solvent evaporation

Sources & evidence

ORD record
ord-f89ae7f850624630b36faacbab08cd8f
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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