Sodium hydride → HCID 68539596, compound

HRID 1441676Notes

Reaction equation

HRID 1441676 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:9](=[O:16])[NH:8][C:5]2=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1>CN(C)C=O>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:22][CH2:21][CH2:20][N:8]1[C:5]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[C:9]1=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 68540948HCID 68540948, compound

Product 1

HCID 68539596HCID 68539596, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-Methyl-spiro[indoline-3,4′-piperidin]-2-one (prepared as in Org. Prep. Proced. Int. (1995), 27(6), 691-694)(0.05 g, 0.023 mmol) was dissolved in dry N,N-dimethylformamide (4.0 mL). To the reaction mixture was then added at 0° C. sodium hydride (60% in mineral oil, 10.0 mg, 0.28 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 (0.048 g, 0.023 mmol). The reaction mixture was stirred at 0° C. for 1 hour, then at room temperature under nitrogen atmosphere for 18 hours. The reaction mixture was then partitioned between water-ice and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a crude oil. The crude oil was purified via flash chromatography (3% methanol/dichloromethane) to yield the title compound as an oil.

Workup

  1. additionTo the reaction mixture was then added at 0° C
  2. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  3. waitat room temperature under nitrogen atmosphere for 18 hours
  4. customThe reaction mixture was then partitioned between water-ice and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-92d758d104df4ab3b26032c33e9de766
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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