Sodium hydride → HCID 58878509, compound

HRID 1441666Notes

Reaction equation

HRID 1441666 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Br:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Br:22])[CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 15442175HCID 15442175, compound

Product 1

HCID 58878509HCID 58878509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-Bromo-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 2.60 mmol) was dissolved in dry N,N-dimethylformamide (10.0 mL). To the reaction mixture was then added at 0° C. sodium hydride (60% in mineral oil, 127.3 mg, 3.18 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0° C. for one hour. To the reaction mixture was then added at 0° C., 2-(2-bromo-ethoxy)-tetrahydro-pyran (0.6 g, 2.86 mmol). The reaction mixture was stirred at 0° C. for one hour, then at room temperature under nitrogen atmosphere for 18 hours. The reaction mixture was then partitioned with water-ice and methylene chloride. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (25% ethyl acetate/hexanes) to yield the title compound as a gum.

Workup

  1. additionTo the reaction mixture was then added at 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for one hour
  3. waitat room temperature under nitrogen atmosphere for 18 hours
  4. customThe reaction mixture was then partitioned with water-ice and methylene chloride
  5. washThe organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. customto yield a crude oil
  10. customThe crude oil was purified via flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ac6793575ee242f2b805f4b906e9b357
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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