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

HRID 712432ノート

反応式

HRID 712432 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-767ef283add74ddd8f96e4ec90081aa8
出典データセット
uspto-grants-2015_11
特許番号
US09181277B2

反応ノート

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