Potassium Hydroxide → 3-(Oxiran-2-yl)pyridine

HRID 704804Notes

Reaction equation

HRID 704804 reaction equation
C(OCCOC1C=CC(CCN)=CC=1)C.[C:16]([NH:26][CH2:27][CH2:28][C:29]1C=C[C:32]([OH:35])=[CH:31][CH:30]=1)(OCC1C=CC=CC=1)=O.[OH-].[K+].CS(OCCOCC)(=O)=O.C(OCCOC1C=CC(CCNC(=O)OCC2C=CC=CC=2)=CC=1)C>CS(C)=O.CO>[O:35]1[CH2:32][CH:31]1[C:30]1[CH:16]=[N:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 14103856Benzyl [2-(4-hydroxyphenyl)ethyl]carbamateHCID 15067105HCID 15067105, compoundHCID 20073190HCID 20073190, compoundHCID 54264530HCID 54264530, compound

Product 1

HCID 133195613-(Oxiran-2-yl)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

from 1.3 g of p-(2-ethoxyethoxy)-phenethylamine (prepared by the reaction of N-carbobenzoxytyramine in DMSO in the presence of potassium hydroxide with ethoxyethyl methanesulfonate and catalytic hydrogenation of the benzyl [p-(2-ethoxyethoxy)]phenethylcarbamate obtained in methanol in the presence of pd/C) and 726 mg of 3-[(RS)-2-oxiranyl]pyridine there were obtained

Sources & evidence

ORD record
ord-12b4ae10d71143e99f23b6e5bce018cb
Source dataset
uspto-grants-1991_01
Patent number
US04988714

Reaction notes

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