Propane sultone → 3-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonic acid

HRID 242087Notes

Reaction equation

HRID 242087 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25]1[CH2:31][S:28](=[O:30])(=[O:29])[O:27][CH2:26]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:26][CH2:25][CH2:31][S:28]([OH:30])(=[O:29])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14264Propane sultoneHCID 24758Sodium hydrideHCID 582462431-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

Product 1

HCID 582463633-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude 1-[1-(4-chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol (3.5 g, 11.22 mmol) was added to a suspension of sodium hydride (60% in mineral oil, 471 mg, 11.79 mmol) in dimethylformamide (25 mL). After stirring for 30 min at room temperature 1,3-propanesultone (1.44 g, 11.79 mmol) was added dropwise. The reaction mixture was stirred over night at room temperature. The dimethylformamide was removed in vacuo. The crude product (8.4 g) was used for the next step without further purification.

Workup

  1. additionwas added dropwise
  2. customThe dimethylformamide was removed in vacuo
  3. customThe crude product (8.4 g) was used for the next step without further purification

Sources & evidence

ORD record
ord-d107030a440a4fcdaa364814be7bf77a
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

Loading…