Methyl vinyl ketone → HCID 59710226, compound

HRID 1864493Notes

Reaction equation

HRID 1864493 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH3:14])[NH:11][C@H:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]([CH:19]=[CH2:20])=[O:18]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH3:14])[N:11]([CH2:20][CH2:19][C:17](=[O:18])[CH3:16])[C@H:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 10822535tert-butyl (3R,5S)-3,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 59710226HCID 59710226, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cis-3,5-dimethylpiperazine-1-carboxylic acid tert-butyl ester (3.00 g; prepared according to the method E. Jon Jacobson et. al.: J. Med. Chemistry. 1999, Vol. 42, 1123-144) in 47 mL chloroform was treated with methylvinylketone (1.7 mL) at room temperature and heated at reflux for two days. The reaction was then concentrated, diluted with THF and heated at reflux for 1 day before purifying by column chromatography (0 to 10% MeOH/DCM) to afford 0.865 g of the title compound as a clear, colorless oil. 1H NMR (CDCl3, 300 MHz) δ ppm 1.08 (d, 2H, J=6.07 Hz), 1.47 (s, 9H), 2.17 (s, 3H), 2.52 (m, 6H), 3.10 (m, 2H), 2.86 (bs, 2H); 13C NMR (CDCl3, 75 MHz) 17.6 (2C), 28.62 (5C), 30.8, 37.34, 42.46, 53.57 (4C), 79.85, 154.49, 208.29.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureat reflux for two days
  4. concentrationThe reaction was then concentrated
  5. additiondiluted with THF
  6. temperatureheated
  7. temperatureat reflux for 1 day
  8. custombefore purifying by column chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-f5d3089480294a6fb11fe4a8f4ded834
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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