tert-Butyl N-[3-(4-methyl-2-pyridyl)prop-2-ynyl]carbamate → tert-Butyl N-[3-(4-methyl-2-pyridyl)propyl]carbamate

HRID 631807Notes

Reaction equation

HRID 631807 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[C:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:3]=1

Participants

5

Reactant 2

HCID 131735426tert-Butyl N-[3-(4-methyl-2-pyridyl)prop-2-ynyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 131735425tert-Butyl N-[3-(4-methyl-2-pyridyl)propyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

The residue of step A was dissolved in absolute ethanol (50 ml). The solution was flushed with argon, and a slurry of Pd/C (9.346 g, 0.325 mmol) in absolute ethanol (20 ml) was added. The resulting suspension was stirred in an athmosphere of hydrogen overnight. The reaction mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by column chromatography (silica, gradient of 1 to 5% methanol containing 7N ammonia in DCM) to yield 1.22 g (5.4 mmol, 84%, two steps). MS(ESI) m/z=251.2 [M+1]+.

Workup

  1. customThe solution was flushed with argon
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe residue was purified by column chromatography (silica, gradient of 1 to 5% methanol containing 7N ammonia in DCM)
  5. customto yield 1.22 g (5.4 mmol, 84%, two steps)

Sources & evidence

ORD record
ord-7f8a6f01ebb949658a89278c0e03ae71
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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