Piperidine → HCID 54502549, compound

HRID 1735693Notes

Reaction equation

HRID 1735693 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:15]([CH2:17][C@@H:18]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:16]>ClCCl>[N:1]1([C:15]([CH2:17][C@@H:18]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 53948551HCID 53948551, compound

Product 1

HCID 54502549HCID 54502549, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of piperidine (0.281 g) and triethylamine (0.304 g) in dichloromethane (10 ml) was added dropwise a solution of benzyl (2R)-2-(chlorocarbonylmethyl)-4-methylvalerate (0.816 g) in dichloromethane (5 ml). The solution was stirred at room temperature for 30 minutes and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate (30 ml), and washed with 7% hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution successively. The organic layer was dried over magnesium sulfate, and concentrated in vacuo to give benzyl (2R)-2-(piperidinocarbonylmethyl)-4-methylvalerate (0.931 g) as an oil.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  3. washwashed with 7% hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution successively
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9bb85ed4c5c74dfbb419bdee466964dd
Source dataset
uspto-grants-1996_07
Patent number
US05538950

Reaction notes

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