Benzyl (5-tert-butyl-1,3-oxazol-2-yl)carbamate → 5-Tert-butyl-1,3-oxazol-2-amine

HRID 1748331Notes

Reaction equation

HRID 1748331 reaction equation
[C:1]([C:5]1[O:9][C:8]([NH:10]C(=O)OCC2C=CC=CC=2)=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([C:5]1[O:9][C:8]([NH2:10])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 14054539Benzyl (5-tert-butyl-1,3-oxazol-2-yl)carbamate

Product 1

HCID 146232945-Tert-butyl-1,3-oxazol-2-amineYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl (5-tert-butyl-1,3-oxazol-2-yl)carbamate (5.0 g, 18.2 mmol) in methanol (100 mL) is added 10% palladium on carbon (500 mg, 0.5 mmol). The reaction is stirred at room temperature for 3 h under hydrogen atmosphere. The reaction mixture is filtered through Celite and the filtrate is concentrated. The residue is purified by flash column chromatography to afford the title compound (1.7 g, 68%) as a light brown solid.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-c8351d8a8e604ec1911bc060e66eade0
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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