Sodium hydride → HCID 21906096, compound

HRID 1246757Notes

Reaction equation

HRID 1246757 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].Br[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1>C(COC)OC.CCOCC>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 15541517tert-Butyl 4-bromopiperidine-1-carboxylateHCID 178418616HCID 178418616, compound

Product 1

HCID 21906096HCID 21906096, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a slurry of sodium hydride (about 60% oil suspension, 397 mg) in dimethoxyethane (4 ml) was added a solution of 2-pyridinethiol (1.05 g) in dimethoxyethane (6 ml) at 0° C., and the mixture was stirred at room temperature for 1 hour. To the mixture was added tert-butyl 4-bromo-1-piperidinecarboxylate (2.74 g), and the mixture was refluxed for 2 hours. After cooling, the resulting suspension was diluted with ether and filtered through a pad of Celite. The filtrate was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; 14% ethyl acetate in n-hexane) to give the title compound (2.2 g) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationfiltered through a pad of Celite
  4. washThe filtrate was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent; 14% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-e59b1e84166f4efea413541442a9599d
Source dataset
uspto-grants-2006_10
Patent number
US07129243B2

Reaction notes

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