(R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester → (R)-4-(3-amino-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester

HRID 19195Notes

Reaction equation

HRID 19195 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][N:14]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[N:15]2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][N:14]2[CH:18]=[CH:17][C:16]([NH2:19])=[N:15]2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 57920020(R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 57920061(R)-4-(3-amino-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl esterYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a Parr shaker bottle was placed (R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester (1.21 g, 3.71 mmol), 10% palladium on carbon (500 mg) and ethanol (25 mL). The bottle was then placed on the Parr shaker at 50 psi of hydrogen pressure for 5 h. The reaction was then filtered through a pad of celite and washed with ethanol and concentrated in vacuo to afford (R)-4-(3-amino-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (1.07 g, 97%) as a yellow oil: LR-ES-MS m/z calculated for C14H24N4O3 [M]+ 296, observed 297 [M+H]+.

Workup

  1. filtrationThe reaction was then filtered through a pad of celite
  2. washwashed with ethanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c35176e1fc9947c9871229668636aab3
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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