Citric Acid → HCID 60064194, compound

HRID 412583Notes

Reaction equation

HRID 412583 reaction equation
[CH:1]([N-]C(C)C)([CH3:3])[CH3:2].[Li+].O1CCCC1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]#[N:28])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(Br)C=C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24]([CH2:3][CH:1]=[CH2:2])([C:27]#[N:28])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7841Allyl bromideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)

Product 1

HCID 60064194HCID 60064194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2M lithium diisopropylamide-tetrahydrofuran solution (9.96 ml) in tetrahydrofuran (20 ml) was dropwise added a solution of 4-cyanopiperidine-1-carboxylic acid tert-butyl ester (3.5 g) in tetrahydrofuran (15 ml) at −78° C. and under argon atmosphere, and the mixture was stirred at room temperature for 30 min. Then, allyl bromide (2.15 ml) was added at −78° C., and the mixture was stirred at the same temperature for 30 min and at room temperature for 1 hour. After completion of the reaction, 10% aqueous citric acid was added and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) and dried under reduced pressure to give the title compound (3.5 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 min and at room temperature for 1 hour
  2. additionwas added
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-cf62eb1bbd8e44c29a9a9c7b1faa1fee
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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