L-Proline → Ethyl 1,4-diazatricyclo[6.3.0.02,6]undecane-4-carboxylate

HRID 1646005Notes

Reaction equation

HRID 1646005 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].[NH:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1C(O)=O>C1(C)C=CC=CC=1>[N:13]12[CH2:20][CH2:19][CH2:18][CH:14]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

4

Reactant 2

HCID 145742L-ProlineHCID 11084330Ethyl allyl(2-oxoethyl)carbamate

Product 1

HCID 53870311Ethyl 1,4-diazatricyclo[6.3.0.02,6]undecane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.6 g (50 mmol) of ethyl N-allyl-N-(2-oxoethyl)-carbamate are heated under reflux overnight with 5.8 g (50 mmol) of proline in 200 ml of toluene. The mixture is concentrated and the residue is distilled.

Workup

  1. concentrationThe mixture is concentrated
  2. distillationthe residue is distilled

Sources & evidence

ORD record
ord-49aae351d151408d8d0a9439d1d2dab0
Source dataset
uspto-grants-1993_01
Patent number
US05177210

Reaction notes

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