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

HRID 2202270ノート

反応式

HRID 2202270 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 59834874cis-3-tert-Butoxycarbonylmethyl-cyclobutanecarboxylic acid収率 99.1%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ef0fe15b66f842709d0e4b747a64ad93
出典データセット
uspto-grants-2016_06
特許番号
US09365520B2

反応ノート

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