Hydrogen Peroxide → HCID 22292837, compound

HRID 2035456Notes

Reaction equation

HRID 2035456 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][C:10](=[CH2:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].B.C1C[O:25]CC1.C([O-])(O)=O.[Na+].OO>O1CCCC1.CCOC(C)=O.O>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH2:12][OH:25])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 22292788N-Trifluoroacetyl-7-methoxy-1-methylene 2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 22292837HCID 22292837, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-trifluoroacetyl-7-methoxy-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine (0.100 g, 0.35 mmol) in tetrahydrofuran (1 mL) was treated with BH3-THF complex (0.36 mL, 1 M in THF), and stirred for 30 min. at 20 C. Water (0.5 mL), saturated aqueous NaHCO3 (0.5 mL), and 30% H2O2 (0.2 mL) were added sequentially and the reaction stirred for 30 min. at 20 C. The product mixture was diluted with to EtOAc (10 mL), washed with brine (10 mL), and concentrated. Flash chromatography (33% EtOAc in hexane, silica) resulted in 0.035 g of a clear oil. MS calculated for C14H16F3NO3+H: 304, observed: 304.

Workup

  1. stirringthe reaction stirred for 30 min. at 20 C
  2. washwashed with brine (10 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cafad1544b87432ab8bfc497fedeb4d4
Source dataset
uspto-grants-2013_11
Patent number
US08575149B2

Reaction notes

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