Ethyl 2,8-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate → 2,8-Dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane

HRID 981106Notes

Reaction equation

HRID 981106 reaction equation
[CH3:1][N:2]1[O:9][CH2:8][CH:7]2[CH:3]1[CH:4]([CH3:15])[N:5](C(OCC)=O)[CH2:6]2>O>[CH3:1][N:2]1[O:9][CH2:8][CH:7]2[CH:3]1[CH:4]([CH3:15])[NH:5][CH2:6]2

Participants

3

Reactant 1

HCID 15070012Ethyl 2,8-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

Product 1

HCID 150700132,8-Dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.2 g (42.9 mmol) of ethyl 2,8-dimethyl-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate are heated under reflux with 23.5 g of Ba(OH)2.8H2O in 235 ml of water overnight. The BaCO3 is filtered off with suction, K2CO3 is added to the filtrate and the solid is filtered off with suction again. The filtrate is extracted ten times with 50 ml of CHCl3 each time, the extracts are dried over K2CO3 and concentrated and the residue is distilled.

Workup

  1. filtrationThe BaCO3 is filtered off with suction, K2CO3
  2. additionis added to the filtrate
  3. filtrationthe solid is filtered off with suction again
  4. extractionThe filtrate is extracted ten times with 50 ml of CHCl3 each time
  5. dry with materialthe extracts are dried over K2CO3
  6. concentrationconcentrated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-d26c949ff4764d1e9307e92481ca66c6
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

Loading…