Hydrochloric Acid → (4aS,7aR)-rel-Octahydropyrrolo[3,4-b][1,4]oxazine dihydrochloride

HRID 374554Notes

Reaction equation

HRID 374554 reaction equation
C([N:8]1[C@@H:16]2[C@@H:12]([CH2:13][NH:14][CH2:15]2)[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:17]>C(O)C.[Pd]>[ClH:17].[ClH:17].[C@@H:12]12[CH2:13][NH:14][CH2:15][C@@H:16]1[NH:8][CH2:9][CH2:10][O:11]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10856960rac-(4aR,7aS)-4-benzyl-octahydropyrrolo[3,4-b]morpholine

Product 1

HCID 22857293(4aS,7aR)-rel-Octahydropyrrolo[3,4-b][1,4]oxazine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

26 g (0.11 mol, 92% strength) of cis-5-benzyl-2-oxa-5,8-diazabicyclo[4.3.0]nonane are hydrogenated on 3 g of palladium/active charcoal (10% Pd) at 100° C. and 100 bar H2 in 180 ml of ethanol and 19 ml of concentrated hydrochloric acid. The catalyst is filtered off with suction, the filtrate is concentrated and the crystals which have separated out are dried in a desiccator over phosphorus pentoxide.

Workup

  1. filtrationThe catalyst is filtered off with suction
  2. concentrationthe filtrate is concentrated
  3. customthe crystals which have separated out
  4. dry with materialare dried in a desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-ccf30365f6c34b6d8d579e5f4381522a
Source dataset
uspto-grants-1996_01
Patent number
US05480879

Reaction notes

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