Cyclohexanecarboxaldehyde → 2-[(tert-butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-3-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester

HRID 639868노트

반응식

HRID 639868 반응식
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]([C:20]1[NH:21][C:22]([O:26][Si](C(C)(C)C)(C)C)=[CH:23][C:24]=1[CH3:25])=[O:19].[CH:34]1([CH:40]=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>ClCCl>[CH3:16][O:17][C:18]([C:20]1([CH:40]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:24]([CH3:25])=[CH:23][C:22](=[O:26])[NH:21]1)=[O:19]

참가 물질

5

반응물 3

HCID 16275CyclohexanecarboxaldehydeHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 575874385-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-1h-pyrrole-2-carboxylic acid methyl ester

생성물 1

HCID 685762772-[(tert-butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-3-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester수율 85.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyldimethylsilyltrifluoromethanesulfonate (2.40 ml, 2.75 g, 10.4 mmol, 2.0 equiv) was added dropwise over 8 min to a stirring solution of 5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-pyrrole-2-carboxylic acid methyl ester (1.4 g, 5.2 mmol, 1.0 equiv) and cyclohexanecarbaldehyde (0.94 ml, 0.87 g, 7.8 mmol, 1.5 equiv) in dichloromethane (100 ml) at −78° C. The resultant solution was stirred at −78° C. for 2 h, then pH=7 buffer solution (50 ml) was added. The organic layer was washed with brine solution (50 ml), and dried over sodium sulfate. The solids were filtered and the filtrate was concentrated. The residue obtained was purified by flash column chromatography (5% ethyl acetate-dichloromethane initially, grading to 8% ethyl acetate-dichloromethane, then to 10% ethyl acetate-dichloromethane) to give 2-[(tert-butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-3-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester (1.69 g, 85%) as a colorless oil.

후처리

  1. washThe organic layer was washed with brine solution (50 ml)
  2. dry with materialdried over sodium sulfate
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue obtained
  6. customwas purified by flash column chromatography (5% ethyl acetate-dichloromethane initially

출처 및 근거

ORD 기록
ord-74a4be04148542ff9fc120b412960eb2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691896B2

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