tert-Butyl piperazine-1-carboxylate → HCID 11486015, compound

HRID 1072430Notes

Reaction equation

HRID 1072430 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C@@H:13]1[CH2:15][O:14]1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:15][C@H:13]([OH:14])[C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 11275682HCID 11275682, compoundHCID 23665649Lithium perchlorate

Product 1

HCID 11486015HCID 11486015, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-2-(6-Methoxyquinolin-4-yl)oxirane (Example 3a) (4.30 g, 21.37 mmol) was dissolved in acetonitrile (30 mL). To the solution was added piperazine-1-carboxylic acid tert-butyl ester (7.17 g, 38.47 mmol) and lithium perchlorate (2.27 g, 106.4 mmol). The resulting slurry was stirred at room temperature for 10 hours and then concentrated in vacuo. The residue was partitioned between ethyl acetate and water and the organic phase dried over magnesium sulfate. Concentration in vacuo afforded a colourless oil which was subjected to purification by column chromatography on silica gel using a dichloromethane/methanol gradient. This provided the desired compound as a colourless oil (7.65 g, 92%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. concentrationConcentration in vacuo
  5. customafforded a colourless oil which
  6. customwas subjected to purification by column chromatography on silica gel using a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-332414ffbed74804ab51d9bd54b128eb
Source dataset
uspto-grants-2005_06
Patent number
US06911442B1

Reaction notes

Loading…