Acetic Acid → 8-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

HRID 1727387ノート

反応式

HRID 1727387 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:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][CH:28]=O.CC(O)=O.[BH3-]C#N.[Na+]>CO>[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][CH2:28][NH: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

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 118461793-(5-fluoro-1H-indol-3-yl)propanalHCID 575676698-amino-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

生成物 1

HCID 160921078-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one収率 82%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 8-amino-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one (1) (200 mg, 0.98 mmol) in anhydrous MeOH (20 ml) was added 3-(5-fluoro-1H-indol-3-yl) propanal (2) (191 mg, 1 mmol), AcOH (0.14 ml), and NaBH3CN (123 mg, 1.96 mmol). Resulting reaction mixture was stirred at room temperature for 2 hr. The solvent was removed in vacuo and the residue was re-dissolved in CH2Cl2 (150 ml). The solution was washed with 1 N NaOH (20 ml) and H2O, Sat. NaCl. The organic solution was separated, dried over Na2SO4, then concentrated in vacuo. The crude compound was purified on silica gel eluting with EtOAc/Hexane (4:1) to yield (3) (304 mg, 82%) as a white solid. MS (APPI) m/z 380.

後処理

  1. customResulting
  2. customreaction mixture
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was re-dissolved in CH2Cl2 (150 ml)
  5. washThe solution was washed with 1 N NaOH (20 ml) and H2O, Sat. NaCl
  6. customThe organic solution was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude compound was purified on silica gel eluting with EtOAc/Hexane (4:1)

出典と根拠

ORDレコード
ord-d250162132a44b63ad0ba4ea44279f4e
出典データセット
uspto-grants-2009_02
特許番号
US07495111B2

反応ノート

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