Sodium hydride → HCID 21906099, compound

HRID 1246752Notes

Reaction equation

HRID 1246752 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.Br[C:18]1[S:19][CH:20]=[CH:21][N:22]=1>C(COC)OC.CCOCC>[S:19]1[CH:20]=[CH:21][N:22]=[C:18]1[O:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 764302-BromothiazoleHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21906099HCID 21906099, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a slurry of sodium hydride (about 60% oil suspension, 5.67 g) in dimethoxyethane (40 ml) was added a solution of tert-butyl 4-hydroxy-1-piperidinecarboxylate (23.9 g) in dimethoxyethane (60 ml) over 30 minutes, and the mixture was stirred for an additional 1 hour. To the mixture was added 2-bromothiazole (15.0 g), and the mixture was refluxed for 4 hours. After cooling, the resulting pale brown suspension was diluted with ether (300 ml) and the mixture was filtered through a pad of Celite. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residual oil was purified by silica gel column chromatography (eluent; 15% ethyl acetate in n-hexane) to give the title compound (22.1 g) as a yellow oil.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered 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 residual oil was purified by silica gel column chromatography (eluent; 15% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-0e8e952962ff4830a786fc62bbb7727d
Source dataset
uspto-grants-2006_10
Patent number
US07129243B2

Reaction notes

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