Sodium ethoxide → (1R,2R,3S,5S)-3-(3,4-Dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo(3.2.1)octane

HRID 1937431Notes

Reaction equation

HRID 1937431 reaction equation
S([C:5]1C=CC(C)=C[CH:6]=1)(O)(=O)=O.[OH:12][CH2:13][C@@H:14]1[C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:19][C@H:18]2[N:29]([CH3:30])[C@@H:15]1[CH2:16][CH2:17]2.[O-]CC.[Na+]>C(O)C>[CH2:5]([O:12][CH2:13][C@@H:14]1[C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:19][C@H:18]2[N:29]([CH3:30])[C@@H:15]1[CH2:16][CH2:17]2)[CH3:6]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86583653HCID 86583653, compound

Product 1

HCID 11370864(1R,2R,3S,5S)-3-(3,4-Dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo(3.2.1)octaneYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(1R, 2R, 3S)-2-hydroxymethyl-3-(3,4-dichlorophenyl)tropane tosylate (2.5 g, 5.5 mmol) was dissolved in anhydrous ethanol (20 ml). Sodium ethoxide in ethanol (2.4 ml, 2.5M, 6 mmol) was added and the reaction mixture was refluxed for 72 hours. The solvent was evaporated off. The residue was stirred with water and ether and extracted three times with ether (3×50 ml) and dried over MgSO4. Evaporation of the solvent yields 1.75 g of the title compound. The product was purified by column chromatography on silica using EtOAc:Et3N (99:1). Yield 1.24 g.

Workup

  1. temperaturethe reaction mixture was refluxed for 72 hours
  2. customThe solvent was evaporated off
  3. extractionextracted three times with ether (3×50 ml)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ae871ae9e3fd4a94b779d62a09a50997
Source dataset
uspto-grants-2002_05
Patent number
US06395748B2

Reaction notes

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