Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]- → cis-3-tert-Butoxycarbonylmethyl-cyclobutanecarboxylic acid

HRID 2202270Notes

Reaction equation

HRID 2202270 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH:7]=[C:8]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6](=[O:15])[CH2:7][CH:8]1[CH2:9][CH:10]([C:12]([OH:14])=[O:13])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59834904Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-

Product 1

HCID 59834874cis-3-tert-Butoxycarbonylmethyl-cyclobutanecarboxylic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(2-(tert-butoxy)-2-oxoethylidene)cyclobutanecarboxylic acid (3.4 g, 16.02 mmol) and 10% palladium-carbon (100 mg, 0.94 mmol, 50%, wet) in MeOH (30 mL) was stirred at room temperature for 5 hr under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 30→100% ethyl acetate/hexane) to give 3-(2-(tert-butoxy)-2-oxoethyl)cyclobutanecarboxylic acid (3.40 g, 15.87 mmol, 99%) as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 30→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ef0fe15b66f842709d0e4b747a64ad93
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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