Water → HCID 69894756, compound

HRID 1356371Notes

Reaction equation

HRID 1356371 reaction equation
C([BH3-])#N.[Na+].O.[OH-].[Na+].Cl.[F:9][C:10]1[CH:11]=[C:12]([C:17]2[C:18]3[C:19]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26][C:20]=4[NH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)[CH:13]=[C:14]([F:16])[CH:15]=1>C(O)(C(F)(F)F)=O.CO>[F:9][C:10]1[CH:11]=[C:12]([C:17]2[C:18]3[C@@H:19]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26][C@@H:20]4[NH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)[CH:13]=[C:14]([F:16])[CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22396744HCID 22396744, compound

Product 1

HCID 69894756HCID 69894756, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 mL 2-neck round-bottomed flask 10-(3,5-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride was dissolved in TFA (3 mL) and cooled to 0° C. A solution of sodium cyanoborohydride (0.084 g, 1.34 mmol) in MeOH was added and the mixture was stirred at room temperature for 2 h. Water was added, followed by 15% NaOH until the pH of the mixture was basic, and the mixture was extracted with EtOAc. The organic layer was concentrated to give 0.21 g of a brown oil. Column chromatography (elution with 2-6% MeOH/chloroform) gave 0.060 g (74%) of the title product as a clear oil: MS (EI) m/z 300 (M+), 300, 256, 255, 244, 243, 242, 240, 229, 201, 56; HRMS (FAB) calcd for C18H18F2N2+H1 301.1516, found 301.1500.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-d90cd96bb615438aadd7a53d34b5292a
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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