147539-53-5 → HCID 21477660, compound

HRID 2293769Notes

Reaction equation

HRID 2293769 reaction equation
[CH3:1][C:2]([CH3:18])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]([CH3:17])([CH3:16])[C:14]#[CH:15])[CH2:9][CH2:8]1)=[O:6])[CH3:3]>C(O)C.[Pt]=O>[CH3:3][C:2]([CH3:18])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]([CH3:17])([CH3:16])[CH2:14][CH3:15])[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

4

Reactant 1

HCID 21477651147539-53-5

Product 1

HCID 21477660HCID 21477660, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A flask is charged with platinum oxide (250 mg) and absolute ethanol (20 ml) and is stirred under a hydrogen atmosphere (balloon) for 1 hr. Then a solution of 1-(1,1-dimethylethoxycarbonyl)-4-(1,1-dimethylprop-2-ynyl)piperazine (PREPARATION 68, 1.77 g) in absolute ethanol (20 ml) is added, and the mixture is stirred under hydrogen (balloon) for 4 hr, filtered, and concentrated. The residue is chromatographed on silica gel (70-230 mesh, 80 g), eluting with ethyl acetate/hexane (25/75), and the appropriate fractions (Rf =0.32, TLC, ethyl acetate/hexane, 25/75) are pooled and concentrated to give the title compound, NMR (CDCl3) 3.38, 2.46, 1.46-1.38, 0.97 and 0.84.

Workup

  1. stirringthe mixture is stirred under hydrogen (balloon) for 4 hr
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (70-230 mesh, 80 g)
  5. washeluting with ethyl acetate/hexane (25/75)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fed9697f6a2940ea9e6f1ecdde824913
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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