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Sodium cyanoborohydride → 9-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

HRID 1727393
ノート
印刷プレビュー

反応式

HRID 1727393 の反応式
[NH2:1][CH:2]1[CH2:16][O:15][C:5]2=[CH:6][CH:7]=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH2:10][CH2:9]3)=[C:4]2[CH2:3]1.[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:27][CH2:28][CH:29]=O.[BH3-]C#N.[Na+]>C(O)(=O)C.CO>[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:27][CH2:28][CH2:29][NH:1][CH:2]1[CH2:16][O:15][C:5]2=[CH:6][CH:7]=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH2:10][CH2:9]3)=[C:4]2[CH2:3]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 3

HCID 5003444Sodium cyanoborohydrideHCID 118461793-(5-fluoro-1H-indol-3-yl)propanalHCID 575676709-amino-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

生成物 1

HCID 462277549-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒
HCID 887
Methanol
溶媒

実験手順

To a mixture of 9-amino-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one (46) (130 mg, 0.596 mmol), 3-(5-fluoro-1H-indol-3-yl)propanal ((2), 113 mg, 0.596 mmol) in acetic acid (70 μl) and methanol (20 ml) was added NaBH3CN (75 mg, 1.19 mmol) in portions. The resulting mixture was stirred for 2 hr. 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. Concentration of organic solution gave the crude compound, which was purified on silica gel (100% EtOAc) to give the desired compound, which was treated with 1 equivalent of etherate HCL to form HCl salt for title compound. MS (APPI) m/z 394.4.

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
  5. customConcentration of organic solution gave the crude compound, which
  6. customwas purified on silica gel (100% EtOAc)

出典と根拠

ORDレコード
ord-6739cf9661714229a53e30ab143d85b7
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

読み込み中…

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