Trifluoroacetic acid → 1-Benzyl-4-[(R)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-3-carboxylic acid methyl ester

HRID 1917281노트

반응식

HRID 1917281 반응식
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:17]([O:24][CH2:25][C@H:26]([CH3:30])/[CH:27]=[CH:28]/[CH3:29])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].FC(F)(F)[C:33](O)=[O:34].O.C(=O)(O)[O-:40].[Na+]>C(Cl)Cl>[CH3:33][O:34][C:29]([CH:28]1[CH:27]([C@@H:26]([CH3:30])[CH2:25][O:24][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14]1)=[O:40]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 86585896Sodium bicarbonate waterHCID 86664645(E)-(R)-5-(tert-Butyldimethylsilyloxy)-4-methylpent-2-ene

생성물 1

HCID 674907991-Benzyl-4-[(R)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-3-carboxylic acid methyl ester수율 69%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (16.6 mL, 65.0 mmol) was added to a solution of (E)-(R)-5-(tert-butyldimethylsilyloxy)-4-methylpent-2-ene acid methyl ester (14 g, 54.2 mmol) in methylene chloride (100 mL), and then a trace amount of trifluoroacetic acid was added. The mixture was stirred for 30 minutes and then saturated sodium bicarbonate water was added. The organic layer was separated and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 14.6 g (69%) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-5cf4918330174b1286454efde22d1e20
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618094B2

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