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

HRID 2202270노트

반응식

HRID 2202270 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ef0fe15b66f842709d0e4b747a64ad93
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365520B2

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