Hydrochloric Acid → rac-(4aR,7aS)-4-benzyl-octahydropyrrolo[3,4-b]morpholine

HRID 1734129Notes

Reaction equation

HRID 1734129 reaction equation
C([N:9]1[CH2:17][C@@H:16]2[C@@H:11]([N:12]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:14][O:15]2)[CH2:10]1)(=O)C1C=CC=CC=1.Cl>O>[CH2:18]([N:12]1[C@@H:11]2[C@@H:16]([CH2:17][NH:9][CH2:10]2)[O:15][CH2:14][CH2:13]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53682667cis-8-Benzoyl-5-benzyl-2-oxa-5,8-diazabicyclo[4.3.0]nonane

Product 1

HCID 10856960rac-(4aR,7aS)-4-benzyl-octahydropyrrolo[3,4-b]morpholine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

91 g (0.265 mol) of cis-8-benzoyl-5-benzyl-2-oxa-5,8-diazabicyclo[4.3.0]nonane with 200 ml of concentrated hydrochloric acid and 140 ml of water are heated under reflux overnight. After cooling, the benzoic acid is filtered off with suction, the solution is reduced to half the volume and made alkaline with potassium carbonate and extracted with chloroform, the extract is dried over potassium carbonate, concentrated and distilled.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. filtrationthe benzoic acid is filtered off with suction
  4. extractionextracted with chloroform
  5. dry with materialthe extract is dried over potassium carbonate
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-3314c8c7bbbe4724b2dad6e1eea99ccd
Source dataset
uspto-grants-1996_07
Patent number
US05532364

Reaction notes

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