HCID 69943268, compound → HCID 69944206, compound

HRID 1978081Notes

Reaction equation

HRID 1978081 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[CH:7][CH2:8][C@H:9]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=[O:12])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[O:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH2:8][C@H:9]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=[O:12])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 69943268HCID 69943268, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69944206HCID 69944206, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.397 g of 4-tert-butyl hydrogen 3(S)-[(tetrahydro-2H-pyran-4-ylidene)ethyl]-2(R)-isobutylsuccinate in 10 ml of methanol was shaken in a hydrogen atmosphere in the presence of 0.196 g of 10% palladium on charcoal catalyst until no further uptake of hydrogen was observed. The catalyst was filtered off and the filtrate was evaporated. There was obtained 0.331 g of 4-tert-butyl hydrogen 3(S)-[(tetrahydro-2H-pyran-4-yl)ethyl]-2(R)-isobutylsuccinate in the form of a colourless gum.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-bbef8ad827b64f0e87393907680de135
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

Loading…