Sodium Bicarbonate → HCID 68430981, compound

HRID 2267129Notes

Reaction equation

HRID 2267129 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:15]([Mg]Br)#[C:16][CH3:17].C(=O)([O-])O.[Na+]>O1CCCC1>[OH:1][C:2]1([C:15]#[C:16][CH3:17])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178419101HCID 178419101, compound

Product 1

HCID 68430981HCID 68430981, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

tert-Butyl 4-oxopiperidine-1-carboxylate (2.99 g) was dissolved in 30 ml of tetrahydrofuran, cooled down to −78° C., 40 ml of a 0.5N solution of 1-propynyl magnesium bromide in 40 ml of tetrahydrofuran was dropped thereinto and temperature of the mixture was raised to room temperature followed by stirring for one night. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction solution to stop the reaction and the product was extracted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride and dried over sodium sulfate. The solvent was evaporated in vacuo and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=4/1) to give 1.41 g of the title compound as a crude product.

Workup

  1. temperaturetemperature of the mixture was raised to room temperature
  2. customthe reaction
  3. extractionthe product was extracted with ethyl acetate
  4. washwashed with a saturated aqueous solution of ammonium chloride
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-fbe7d66ef44f4f3ea57974a034a956a7
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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