HCID 57656071, compound → HCID 57656558, compound

HRID 911416Notes

Reaction equation

HRID 911416 reaction equation
C[O:2][C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[CH3:20]>C(Cl)Cl>[OH:2][C:3]1[C:13]2[CH2:12][CH2:11][N:10]([C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[CH3:20]

Participants

3

Reactant 1

HCID 57656071HCID 57656071, compound

Product 1

HCID 57656558HCID 57656558, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Add borontribromide (21.6 mL, 1.0 M solution in DCM) to a solution of 6-methoxy-7-methyl-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (3.1 g, 10.8 mmol) in DCM (200 mL) at 0° C. under nitrogen. Warm to room temperature and stir overnight. Dilute with DCM and wash with water. Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain the desired intermediate as a solid (2.74 g, 93%). MS (ES+) m/z: 274 (M+H)+.

Workup

  1. washwash with water
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

Sources & evidence

ORD record
ord-b39f25abb5e44b819c7e7acd8b6de22d
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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