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 36686Notes

Reaction equation

HRID 36686 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-382fd6d71893401b82ac7f63aa2dec0a
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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