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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1937432Generated: November 1, 2026

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

https://huagongshe.com/reaction/1937432

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
ReactantEthyl sulfate anionHCID 3804841—
ReactantHCID 68469855HCID 68469855—
SolventTetrahydrofuranHCID 8028—
Product(1R,2R,3S,5S)-3-(3,4-Dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo(3.2.1)octaneHCID 11370864111.1%

Reaction Conditions

Temperature35 °C

Reaction Steps

(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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06395748B2
Source datasetuspto-grants-2002_05
ORD IDord-bd0705460c704a81a090d526ead1f9e8
Source noteuspto-grants-2002_05