Water → Ethyl 1,4-diazatricyclo [6.2.0.02,6]decane-4-carboxylate

HRID 1646003Notes

Reaction equation

HRID 1646003 reaction equation
[CH2:1]([N:4]([CH2:10][CH:11]=O)[C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH:2]=[CH2:3].O.[NH:14]1[CH2:17][CH2:16][CH:15]1C(O)=O>C1(C)C=CC=CC=1>[N:14]12[CH2:17][CH2:16][CH:15]1[CH2:3][CH:2]1[CH:11]2[CH2:10][N:4]([C:5]([O:6][CH2:7][CH3:8])=[O:9])[CH2:1]1

Participants

5

Reactant 3

HCID 962WaterHCID 17288Azetidinecarboxylic AcidHCID 11084330Ethyl allyl(2-oxoethyl)carbamate

Product 1

HCID 54190177Ethyl 1,4-diazatricyclo [6.2.0.02,6]decane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

17.1 g (0.1 mol) of ethyl N-allyl-N-(2-oxoethyl)-carbamate are heated under reflux overnight in a water separator with 10 g (0.1 mol) of azetidine-2-carboxylic acid in 200 ml of toluene. Unreacted amino acid is filtered off with suction, the filtrate is concentrated and the residue is distilled.

Workup

  1. filtrationUnreacted amino acid is filtered off with suction
  2. concentrationthe filtrate is concentrated
  3. distillationthe residue is distilled

Sources & evidence

ORD record
ord-65e950eb01954877b28171df6385e628
Source dataset
uspto-grants-1993_01
Patent number
US05177210

Reaction notes

Loading…