Isopropyl iodide → HCID 68820414, compound

HRID 734333Notes

Reaction equation

HRID 734333 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][C@@H:19]([CH3:23])[CH2:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:24](I)([CH3:26])[CH3:25]>CC#N.CCOC(C)=O>[CH:24]([N:20]1[CH2:21][CH2:22][N:17]([C:15]([O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:16])[CH2:18][CH:19]1[CH3:23])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 7578289Benzyl (3S)-3-methylpiperazine-1-carboxylate

Product 1

HCID 68820414HCID 68820414, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (11.2 g) was added to a solution of (S)-1-benzyloxycarbonyl-3-methylpiperazine (D19)(10.18 g) in CH3CN (60 ml), followed by isopropyl iodide (11.3 ml) and the mixture was heated at reflux overnight. The reaction mixture was then allowed to cool to rt and the inorganics were filtered off. The filtrate was evaporated to give an oil which was taken up in EtOAc (100 ml) and washed with water (2×50 ml). The EtOAc layer was dried (MgSO4) and concentrated to give the title compound (D26) as an oil (8 g). LCMS electrospray (+ve) 277 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationthe inorganics were filtered off
  4. customThe filtrate was evaporated
  5. customto give an oil which
  6. washwashed with water (2×50 ml)
  7. dry with materialThe EtOAc layer was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a111fd71d6fc4db98f41f74e32b3a395
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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