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 1727391Notes

Reaction equation

HRID 1727391 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: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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-aab4cf6ab1cd4568ab4aaaca2bc25db0
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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