Ammonium Hydroxide → HCID 57559135, compound

HRID 736099Notes

Reaction equation

HRID 736099 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[C:10](=[O:20])[CH2:9][N:8]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2].[BH3-]C#N.[Na+].[OH-].[NH4+]>CCO.CC(O)=O>[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[CH:10]([OH:20])[CH2:9][N:8]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 57559126HCID 57559126, compound

Product 1

HCID 57559135HCID 57559135, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 3-(4-fluorobenzoyl)-1-oxo-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (784 mg, 2 mmol) in EtOH (11 mL) and AcOH (3 mL) was added NaBH3CN (500 mg, 8 mmol) and the mixture was stirred at 20° C. overnight. It was then basified with 28% ammonium hydroxide and extracted with DCM. The combined organic layer was washed with water and dried over MgSO4. Evaporation of solvent gave a crude product, which was purified by column chromography on silica gel and eluted with MeOH-DCM (1:19) to give the title compound (450 mg); 1H-NMR (CDCl3): δ 9.61 (1H, s), 8.41 (1H, m), 7.41 (1H, m), 7.25-7.36 (5H, m), 7.05 (2H, m), 4.93 (1H, m), 4.57 (1H, d), 4.42 (3H, m), 3.85 (1H, m), 1.35 (3H, d). MS (ES): 395 (MH+).

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. customEvaporation of solvent
  5. customgave a crude product, which
  6. customwas purified by column chromography on silica gel
  7. washeluted with MeOH-DCM (1:19)

Sources & evidence

ORD record
ord-04b94bb4ea5843648814024a2380e2b9
Source dataset
uspto-grants-2009_09
Patent number
US07595311B2

Reaction notes

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