5-(Azidomethyl)-3-benzyl-1,3-oxazolidin-2-one → (5R)-5-(aminomethyl)-3-benzyl-1,3-oxazolidin-2-one

HRID 2066815Notes

Reaction equation

HRID 2066815 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=[N+]=[N-].[H][H]>[Pd].CO>[NH2:1][CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 722765615-(Azidomethyl)-3-benzyl-1,3-oxazolidin-2-one2×HCID 178418361HCID 178418361, compound

Product 1

HCID 28258715(5R)-5-(aminomethyl)-3-benzyl-1,3-oxazolidin-2-oneYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 40 ml vial was charged with 5-(azidomethyl)-3-benzyl-1,3-oxazolidin-2-one (100 mg, 0.43 mmol, INTERMEDIATE 14), palladium on carbon (5 mg), and methanol (15 ml). The reduction was effected using a balloon filled with hydrogen at room temperature overnight. The catalyst was removed through filtration on a pad of Celite pre-rinsed with methanol. The Celite pad was further rinsed with methanol (2×5 ml) and the eluent concentrated in vacuo to provide 75 mg (85%) of the title compound. Mass spectrum (ESI) 207.2 (M+1).

Workup

  1. customThe catalyst was removed through filtration on a pad of Celite
  2. washpre-rinsed with methanol
  3. washThe Celite pad was further rinsed with methanol (2×5 ml)
  4. concentrationthe eluent concentrated in vacuo

Sources & evidence

ORD record
ord-85c049d52fa849549ca716c04dadf485
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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