Methanol → HCID 66868903, compound

HRID 1850874Notes

Reaction equation

HRID 1850874 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21]C)[CH:19]=4)[CH2:14][CH2:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.B(Br)(Br)Br.CO.C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([OH:21])[CH:19]=4)[CH2:14][CH2:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 66868912HCID 66868912, compound

Product 1

HCID 66868903HCID 66868903, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclopropyl]-7-methoxy-3,4-dihydroisoquinoline (700 mg, 2.2 mmol) in methylenehloride (10 ml) under nitrogen was cooled to −78° C. Borontribromide (BBr3, 4.2 ml 1M in methyleneloride, 4.2 mmol) was added dropwise. The reaction was allowed to warm up to room temperature and stirred overnight. Methanol was added (5 ml) and the resulting mixture poured into water neutralized with 1M sodiumbicarbonate and extracted consecutively with methylenehloride and water. The organic layer was dried (Na2SO4), the solvents removed and the black residue purified by chromatography. Yield: 320 mg, (1.1 mmol, 48%).

Workup

  1. extractionextracted consecutively with methylenehloride and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvents removed
  4. customthe black residue purified by chromatography

Sources & evidence

ORD record
ord-53ae4c32c77c44578b07cec2bd24d884
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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