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

HRID 612376Notes

Reaction equation

HRID 612376 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-d8017782939f43f5b16284293cab8143
Source dataset
uspto-grants-1999_12
Patent number
US06004956

Reaction notes

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