Trifluoroacetic acid → 2-Benzylhexahydropyrano[3,4-c]pyrrol-4(1H)-one

HRID 712432노트

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HRID 712432 반응식
[O:1]1[CH2:6][CH2:5][CH:4]=[CH:3][C:2]1=[O:7].CO[CH2:10][N:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12][Si](C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:17]([N:11]1[CH2:12][CH:4]2[CH2:5][CH2:6][O:1][C:2](=[O:7])[CH:3]2[CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5206605,6-Dihydro-2H-pyran-2-one

생성물 1

HCID 34744972-Benzylhexahydropyrano[3,4-c]pyrrol-4(1H)-one수율 82.87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 5,6-dihydro-2H-pyran-2-one (1.00 g, 1 eq) in CH2Cl2 (150 mL) was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (1.2 eq). After the mixture was cooled to 0° C., a solution of TFA in CH2Cl2 (0.1 eq, 1M) was added slowly. The reaction mixture was slowly heated to room temperature and stirred for 6 h. The reaction mixture was washed with water and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to give the title compound as colorless oil (1.95 g, 82.87%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 232.3 (M+1).

후처리

  1. temperatureThe reaction mixture was slowly heated to room temperature
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA)

출처 및 근거

ORD 기록
ord-767ef283add74ddd8f96e4ec90081aa8
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181277B2

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