Benzyl 2-(oxazol-2-yl)propan-2-ylcarbamate → alpha,alpha-Dimethyl-2-oxazolemethanamine

HRID 631963Notes

Reaction equation

HRID 631963 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([NH:9]C(=O)OCC1C=CC=CC=1)([CH3:8])[CH3:7].[H][H]>C(O)C.[Pd]>[CH3:7][C:6]([CH3:8])([C:2]1[O:1][CH:5]=[CH:4][N:3]=1)[NH2:9]

Participants

5

Reactant 2

HCID 71087227Benzyl 2-(oxazol-2-yl)propan-2-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 82418817alpha,alpha-Dimethyl-2-oxazolemethanamineYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 2-(oxazol-2-yl)propan-2-ylcarbamate (0.63 g, 24 mmol) and palladium 10% on carbon (0.06 g) in ethanol (20 mL) was charged with hydrogen balloon and stirred at room temperature for 2 h. TLC showed the reaction was completed; it was filtered and concentrated to give a yellow oil (0.1 g, 33%); MS: m/e 127.1 [M+H]+. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, 1H, J=0.6 Hz), 7.02 (s, 1H), 2.56 (bs, 4H), 1.59 (s, 6H).

Workup

  1. filtrationit was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-301f235256a94e85a648bc745233bb7e
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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