Iodoethane → HCID 67331813, compound

HRID 1942556Notes

Reaction equation

HRID 1942556 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:19]=2)[CH2:16][CH2:15][N:14]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:41](I)[CH3:42].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]([CH2:41][CH3:42])[C@@H:12]1[C@@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:19]=2)[CH2:16][CH2:15][N:14]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67330469HCID 67330469, compound

Product 1

HCID 67331813HCID 67331813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (rac.)-(3R,4R)-3-{[(benzyloxy)carbonyl]amino}-4-[3-(benzyloxy)-phenyl]piperidine-1-carboxylate (3.70 g) in DMF (16 ml) was added at 0° C. sodium hydride (573 mg), and the mixture was stirred for 15 minutes. To the mixture was added ethyl iodide (1.48 ml), and the mixture was stirred at 60° C. for 5 hours. The reaction solution was cooled, and a saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous ammonium chloride solution (×2) and a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=3/1) to give the title compound (2.59 g).

Workup

  1. stirringthe mixture was stirred at 60° C. for 5 hours
  2. temperatureThe reaction solution was cooled
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous ammonium chloride solution (×2)
  5. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-2d879a2878ed4aaf861d41d5788ae957
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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