HCID 22875336, compound → rac-tert-Butyl (4aR,7aS)-octahydropyrrolo[3,4-b]morpholine-6-carboxylate(WX110023)

HRID 2256091Notes

Reaction equation

HRID 2256091 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([N:11](N[C@@H](C3C=CC=CC=3)C)[CH2:12][CH2:13][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([NH:11][CH2:12][CH2:13][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22875336HCID 22875336, compound

Product 1

HCID 22875335rac-tert-Butyl (4aR,7aS)-octahydropyrrolo[3,4-b]morpholine-6-carboxylate(WX110023)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of 417 mg of cis-8-tert-butoxycarbonyl-5-[(1R)-1-phenylethylamino]-2-oxa-5,8-diazabicyclo[4.3.0]nonane 14a and 200 mg of 10% palladium on charcoal in 50 ml of ethanol was shaken under a pressured hydrogen atmosphere of 4.5 kg/cm2 for 4 hours. Then further 100 mg of 10% palladium on charcoal was added and hydrogenation was carried out under the above-mentioned condition. Throughout the reaction, the reaction vessel was heated by irradiation with a tungsten lamp. The catalyst was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was subjected to silica gel column chromatography. From an eluant of chloroform containing 10% methanol, the titled compound 15a weighing 286 mg was obtained.

Workup

  1. customThroughout the reaction
  2. temperaturethe reaction vessel was heated by irradiation with a tungsten lamp
  3. customThe catalyst was removed by filtration
  4. customthe solvent of the filtrate was removed under reduced pressure
  5. customwas obtained

Sources & evidence

ORD record
ord-c0286a802d0944108910c4a8a4a43e1b
Source dataset
uspto-grants-1997_08
Patent number
US05654318

Reaction notes

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