Methanol → HCID 66868903, compound

HRID 242094Notes

Reaction equation

HRID 242094 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 sodiumbi-carbonate 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-c2f36b9dbe854295ab0d94ba98a1bb52
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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