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

HRID 1937432Notes

Reaction equation

HRID 1937432 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:8][C@H:7]2[N:18]([CH3:19])[C@@H:4]1[CH2:5][CH2:6]2.[H-].[Na+].[CH2:22](OS([O-])(=O)=O)[CH3:23].O>C1COCC1>[CH2:22]([O:1][CH2:2][C@@H:3]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:8][C@H:7]2[N:18]([CH3:19])[C@@H:4]1[CH2:5][CH2:6]2)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3804841Ethyl sulfate anionHCID 68469855HCID 68469855, compound

Product 1

HCID 11370864(1R,2R,3S,5S)-3-(3,4-Dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo(3.2.1)octaneYield 111.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

(1R, 2R, 3S)-2-hydroxymethyl-3(3,4-dichlorophenyl)tropane (26.9 g, 0.09 mol) in THF (200 ml) was added sodium hydride 60% in oil (4.6 g, 0.12 mol) and ethylsulphate (15.7 ml, 0.12 mol) and heated to 30-40° C. on an oil bath for ½ hour. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture is then heated to 30-40° C. on an oil bath for 1 hour and poured into water (500 ml). The mixture was extracted twice with tert.butylmethylether, the organic phases was washed with water and dried over MgSO4 and evaporated to yield the 32.82 g of the title compound.

Workup

  1. temperatureThe reaction mixture is then heated to 30-40° C. on an oil bath for 1 hour
  2. extractionThe mixture was extracted twice with tert.butylmethylether
  3. washthe organic phases was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-bd0705460c704a81a090d526ead1f9e8
Source dataset
uspto-grants-2002_05
Patent number
US06395748B2

Reaction notes

Loading…