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Acetic Acid → 8-{[(6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl]amino}-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

HRID 1727391
ノート
印刷プレビュー

反応式

HRID 1727391 の反応式
[NH2:1][CH:2]1[CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]3[CH2:8][NH:7][C:6](=[O:15])[C:5]=3[C:4]=2[CH2:3]1.[F:16][C:17]1[CH:18]=[C:19]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]1[CH2:24][CH2:23][CH:22]([CH:30]=O)[CH2:21][C:20]2=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[F:16][C:17]1[CH:18]=[C:19]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]1[CH2:24][CH2:23][CH:22]([CH2:30][NH:1][CH:2]3[CH2:14][O:13][C:12]4[CH:11]=[CH:10][C:9]5[CH2:8][NH:7][C:6](=[O:15])[C:5]=5[C:4]=4[CH2:3]3)[CH2:21][C:20]2=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 251395066-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carbaldehydeHCID 575676698-amino-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

生成物 1

HCID 690616378-{[(6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl]amino}-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of (1) (60 mg, 0.294 mmol), 6-fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carbaldehyde ((28), 64 mg, 0.294 mmol) in acetic acid (38 mg, 0.588 mmol) and methanol (3 ml) was added NaBH3CN (37 mg, 0.588 mmol) in portions. The resulting mixture was stirred for 40 min. The solvent was removed in vacuo and the residue was dissolved in methylene chloride. The organic solution was washed with 1N NaOH and saturated NaCl before being dried over with Na2SO4. The concentration of organic solution in vacuo gave crude (27), which was purified on silica gel eluting with 80% EtOAc/Hexane to give a white solid (71 mg, 60%). MS (ES) m/z 406.2

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe organic solution was washed with 1N NaOH and saturated NaCl
  4. dry with materialbefore being dried over with Na2SO4

出典と根拠

ORDレコード
ord-aab4cf6ab1cd4568ab4aaaca2bc25db0
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07495111B2

反応ノート

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