Water → HCID 86613108, compound

HRID 645386Notes

Reaction equation

HRID 645386 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[B-](F)(F)(F)[F:21].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.FC(F)(F)S(O)(=O)=O.O>ClCCCl>[F:19][C:2]([F:18])([F:1])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[C:13]([F:21])=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 2724933SelectfluorHCID 86613107HCID 86613107, compound

Product 1

HCID 86613108HCID 86613108, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

A solution of (S)-N-trifluoroacetyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (2.5 g, 8.5 mmol) in 1,2-dichloroethane (15 mL) was treated with Selectfluor (3.9 g, 11 mmol), trifluoromethanesulfonic acid (8 mL, 90 mmol) and stirred 60 hours at 75° C. The product mixture was poured into water (200 mL), extracted with EtOAc (200 mL), the organic phase washed with saturated aqueous NaHCO3 (2×100 mL), brine (100 mL), dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography (6% EtOAc in hexane, silica) resulting in 0.6 g of a white solid. MS calculated for C13H12ClF4NO+H: 310, observed: 310.

Workup

  1. extractionextracted with EtOAc (200 mL)
  2. washthe organic phase washed with saturated aqueous NaHCO3 (2×100 mL), brine (100 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (6% EtOAc in hexane, silica)

Sources & evidence

ORD record
ord-350dd51e9bea4e12a4a00bd6f11b8376
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

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