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Acetic Acid → 8-{[4-(5-fluoro-1H-indol-3-yl)butyl]amino}-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

HRID 1727390
Notes
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Reaction equation

HRID 1727390 reaction equation
[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][CH2:28][CH:29]=O.C(O)(=O)C.[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][CH2:29][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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 118460104-(5-fluoro-1H-indol-3-yl)butanalHCID 575676698-amino-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

Product 1

HCID 462253108-{[4-(5-fluoro-1H-indol-3-yl)butyl]amino}-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-oneYield 78%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Procedure

To a mixture of (1) (60 mg, 0.294 mmol), 4-(5-fluoro-1H-indol-3-yl)butanal (21), 63 mg, 0.294 mmol) in acetic acid (37 μl, 0.62 mmol) and methanol (4 ml) was added NaBH3CN (37 mg, 0.588 mmol) in portions. Resulting mixture was stirred for 1.5 hr. The solvent was removed in vacuo and the residue was dissolved in CH2Cl2 and washed with 1 N NaOH and saturated NaCl. The organic solution was dried over Na2SO4 and concentrated in vacuo. The compound was purified on silica gel eluting with 60% EtOAc/Hexane to give (25) as a solid (90 mg, 78%). MS (ES) m/z 394.2;

Workup

  1. customResulting mixture
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washwashed with 1 N NaOH and saturated NaCl
  5. dry with materialThe organic solution was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe compound was purified on silica gel eluting with 60% EtOAc/Hexane

Sources & evidence

ORD record
ord-5874ff6b482d4599ac6e679eaac3dbd0
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495111B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes