7-Benzyl-1-tert-butoxycarbonylaminomethyl-2-oxa-7-azabicyclo[3.3.0]octane → 1-Tert-butoxycarbonylaminomethyl-2-oxa-7-aza-bicyclo[3.3.0]octane

HRID 53878Notes

Reaction equation

HRID 53878 reaction equation
C([N:8]1[CH2:15][C:14]2([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:10]([CH2:11][CH2:12][O:13]2)[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[C:21]([O:20][C:18]([NH:17][CH2:16][C:14]12[CH2:15][NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][O:13]2)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 217047517-Benzyl-1-tert-butoxycarbonylaminomethyl-2-oxa-7-azabicyclo[3.3.0]octane

Product 1

HCID 217047491-Tert-butoxycarbonylaminomethyl-2-oxa-7-aza-bicyclo[3.3.0]octane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

12.2 g (34.5 mmol) of 7-benzyl-1-tert-butoxycarbonylaminomethyl-2-oxa-7-aza-bicyclo[3.3.0]octane are hydrogenated in 200 ml of ethanol on 7 g of palladium-active charcoal (10% Pd) at 100° C. and 100 bar. The catalyst is filtered off with suction and the filtrate is concentrated and distilled. Yield: 5.7 g (68% of theory) Boiling point: 120°-130° C./0.01 mbar.

Workup

  1. filtrationThe catalyst is filtered off with suction
  2. concentrationthe filtrate is concentrated
  3. distillationdistilled

Sources & evidence

ORD record
ord-c143780869ab4d41ab651f0a337b60ed
Source dataset
uspto-grants-1997_04
Patent number
US05621105

Reaction notes

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