HCID 86727023, compound → HCID 85248869, compound

HRID 1472227Notes

Reaction equation

HRID 1472227 reaction equation
C([O:8][CH2:9][CH:10]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[Si:20]([O:19][CH:10]([CH2:9][OH:8])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([C:23]([CH3:25])([CH3:26])[CH3:24])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 86727023HCID 86727023, compound

Product 1

HCID 85248869HCID 85248869, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(benzyloxy)-3-(tert-butyldimethylsilyloxy) butanoate XXXVI (3.1 g, 8.15 mmol) in EtOAc (200 mL) under a nitrogen atmosphere was added 10% palladium on carbon (600 mg). The reaction flask was evacuated and then charged with a balloon of hydrogen. The reaction mixture was then stirred at room temperature for 16 h before being filtered through Celite. The filtrate was then concentrated under reduced pressure. Purification of the crude product by column chromatography (100% DCM→50% EtOAc/DCM) afforded tert-butyl 3-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate XXXVII (2.1 g, 7.22 mmol, 88.7% yield) as a colorless oil.

Workup

  1. customThe reaction flask was evacuated
  2. additioncharged with a balloon of hydrogen
  3. filtrationbefore being filtered through Celite
  4. concentrationThe filtrate was then concentrated under reduced pressure
  5. customPurification of the crude product by column chromatography (100% DCM→50% EtOAc/DCM)

Sources & evidence

ORD record
ord-0c70d54dec8b4fdfb21e22cf5292da1c
Source dataset
uspto-grants-2015_04
Patent number
US09012491B2

Reaction notes

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