7-(Benzyloxy)-1-[1-(4-chloro-2-methoxyphenyl)cyclobutyl]-3,4-dihydroisoquinoline → 1-[1-(4-Chloro-2-methoxyphenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

HRID 242079Notes

Reaction equation

HRID 242079 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]=[C:16]2[C:19]2([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[O:30][CH3:31])[CH2:22][CH2:21][CH2:20]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>Br.C(O)(=O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:19]2([C:16]3[C:17]4[C:12](=[CH:11][CH:10]=[C:9]([OH:8])[CH:18]=4)[CH2:13][CH2:14][N:15]=3)[CH2:20][CH2:21][CH2:22]2)=[C:24]([O:30][CH3:31])[CH:25]=1

Participants

4

Reactant 1

HCID 582462497-(Benzyloxy)-1-[1-(4-chloro-2-methoxyphenyl)cyclobutyl]-3,4-dihydroisoquinoline

Product 1

HCID 582462641-[1-(4-Chloro-2-methoxyphenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

7-(benzyloxy)-1-[1-(4-chloro-2-methoxyphenyl)cyclobutyl]-3,4-dihydroisoquinoline (460 mg, 1.065 mmol) were dissolved in 33% hydrobromic acid in acetic acid. The reaction mixture was stirred at room temperature for 15 min. The solvent was evaporated in vacuo. Toluene was added and evaporated in vacuo (repeated three times). The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:methanol=4:1). Yield: 322 mg (0.942 mmol, 88%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionToluene was added
  3. customevaporated in vacuo (repeated three times)
  4. customThe crude product was purified by flash chromatography (silica, dichloromethane

Sources & evidence

ORD record
ord-847dfc25dca9461eb6cc61c04c5e32ea
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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