Methanol → (2S,3R)-methyl 3-amino-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

HRID 1783439Notes

Reaction equation

HRID 1783439 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([O:18][CH3:19])=[O:17])=[N+]=[N-].CO>C(O)(C(F)(F)F)=O.[Pd].O1CCOCC1>[NH2:1][C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:14])([CH3:15])[CH3:13])([CH3:10])[CH3:11])[C@@H:5]1[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 2

HCID 887MethanolHCID 57589884(2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Product 1

HCID 57589866(2S,3R)-methyl 3-amino-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidCatalystHCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 132 (5.85 mmol) in 3:1 methanol:dioxane (25 mL) was added a few drops of TFA and 10% Pd/C (10 wt %). The reaction was stirred under atmospheric hydrogen for one hour and then filtered through Celite. The solvent was removed and the residue triturated with diethyl ether to afford 133, which was used in the next step without further purification.

Workup

  1. filtrationfiltered through Celite
  2. customThe solvent was removed
  3. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-d28195f9c9524fe4962bc858c6a23a46
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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