[2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl ester → 2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine

HRID 1480127

Reaction equation

HRID 1480127 reaction equation
C(OC(=O)[NH:10][C:11]([CH3:22])([C:16]1[N:20]=[C:19]([CH3:21])[O:18][N:17]=1)[CH2:12][CH:13]1[CH2:15][CH2:14]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH:13]1([CH2:12][C:11]([NH2:10])([CH3:22])[C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 90203645[2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 710877912-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamineYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of [2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid benzyl ester (Example 66d, 540 mg, 1.71 mmol) in ethanol (10 ml) under argon atmosphere was added palladium on charcoal 10% (54.7 mg, 514 μmol). The reaction was stirred at room temperature under a pressure of 2.5 bar hydrogen for 2 hours. The reaction mixture was filtered through a pad celite and the filter cake was washed two times with ethanol. The filtrate was evaporated down to dryness to yield the title compound (163 mg, 53%) as crude yellow oil which was used with any purification. MS (ESI, m/z): 182.2 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad celite
  2. washthe filter cake was washed two times with ethanol
  3. customThe filtrate was evaporated down to dryness

Sources & evidence

ORD record
ord-1eedee4e648f458f98d23c07f2345db9
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Linked notes

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