HCID 69949538, 화합물 → 4-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester

HRID 2298965노트

반응식

HRID 2298965 반응식
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]([O:17]C(C)(C)C)=[O:16])[CH2:10][CH2:9]1)=[O:7])(C)(C)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])[CH3:2]

참가 물질

5

반응물 2

HCID 69949538HCID 69949538, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 158961924-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester수율 99.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of diester (B) (12.5 g, 46.3 mmol) and 10% palladium on activated carbon (5 g) in absolute ethanol (200 mL) was exposed to a hydrogen atmosphere (at balloon pressure) and stirred vigorously for 1 h. After removal of catalyst by filtration and concentration, the resultant colorless oil was dissolved in methylene chloride (150 mL) and TFA (75 mL) and stirred for 15 min. All volatiles were removed by rotary evaporation and the resultant colorless oil placed under high vacuum to give (C) 4-carboxymethyl-cyclohexanecarboxylic acid ethyl ester (9.9 g, 99%) as a white solid. Data for cis/trans mixture: 1H NMR (400 MHz, CD3OD) δ4.13 (2q, 4 H), 2.58 (m, 1H), 2.30-2.20 (m, 1 H), 2.20 (2d, 4 H), 2.05-1.80 (m, 7 H), 1.80-1.55 (m, 5 H), 1.50-1.38 (m, 3 H), 1.32-1.25 (m, 1 H), 1.25 (2t, 6 H), 1.10-1.00 (m, 2 H); mass spectrum m/z 215 [(M+H)+; calcd for C11H19O4: 215].

후처리

  1. customAfter removal of catalyst
  2. filtrationby filtration and concentration
  3. dissolutionthe resultant colorless oil was dissolved in methylene chloride (150 mL)
  4. stirringTFA (75 mL) and stirred for 15 min
  5. customAll volatiles were removed by rotary evaporation

출처 및 근거

ORD 기록
ord-4eae9c3e84fc40fb8eb38ab3fffa9aa5
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495561B2

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