Ethyl Acetate → HCID 59504743, compound

HRID 2400558Notes

Reaction equation

HRID 2400558 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[CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.C(OCC)(=O)C>C1COCC1>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([CH2:18][O:3][CH:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]2)=[CH:20][CH:21]=1)#[N:24]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 59504743HCID 59504743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil; 490 mg, 12.2 mmol) in THF (10 mL) was added a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (2.46 g, 12.2 mmol) in THF (2 mL) at rt. The reaction mixture was stirred at rt for several minutes and then heated to reflux for 15 min. After cooling to rt 4-(bromomethyl)benzonitrile (2.00 g, 10.2 mmol) was added, and the reaction mixture was stirred at rt over night. Ethyl acetate was added and the mixture was washed with water. The organic layer was dried with anhydrous magnesium sulfate and filtered. The solvent was removed and the crude product was used as such for Step 2.

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 min
  3. additionwas added
  4. stirringthe reaction mixture was stirred at rt over night
  5. washthe mixture was washed with water
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-12b5f20a6f0041699eae2a0675704d46
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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