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

HRID 129429Notes

Reaction equation

HRID 129429 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.C(O)(=O)C1C=CC=CC=1>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

5

Reactant 3

HCID 243Benzoic AcidHCID 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 are refluxed overnight with 200 ml of concentrated hydrochloric acid and 140 ml of water. The batch is cooled and the benzoic acid suctioned off. The batch is concentrated to half its original volume, adjusted to alkalinity with potassium carbonate, extracted with chloroform, dried over potassium carbonate, concentrated, and distilled.

Workup

  1. temperatureThe batch is cooled
  2. concentrationThe batch is concentrated to half its original volume
  3. extractionextracted with chloroform
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-e4fddf6a3d634a8ea900c4f13e228d4e
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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