Sodium Hydroxide → 1246390-08-8

HRID 2189972Notes

Reaction equation

HRID 2189972 reaction equation
C([O:3][C:4]([C:6]1([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].C(OCC)(=O)C.C1COCC1>CCO>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21939870Tetrahydrofuran ethyl acetateHCID 59527933HCID 59527933, compound

Product 1

HCID 595278831246390-08-8

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 250 mL round bottom flask with a magnetic stirrer, 5.4 g (16.7 mmol) 4-cyclopentyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester was dissolved in 40 mL EtOH. To the colourless solution 40 mL 4N NaOH was added. The orange solution was stirred under reflux for total of 6 days. The ethanol was removed and the reaction mixture was diluted with 100 mL ice water and extracted twice with 100 mL diethyl ether. The aqueous layer was acidified with 60 mL 4 N HCl to pH=2. A white precipitate formed and after addition of 200 mL ethyl acetate: THF 1:1 the white gelatinous suspension was filtered through a membrane filter. The aqueous layer from the filtrate was separated and extracted once with 100 mL ethyl acetate. The organic was layer dried with Na2SO4, filtered and concentrated under vacuum. The crude product (2.54 g, yellow viscous oil) was purified over silica chromatography eluting with a gradient formed from heptane and ethyl acetate to yield after evaporation of the product containing fractions 1.89 g (38%) of the title compound as off-white solid. MS ISP (m/e): 298.2 [(M+H)+].

Workup

  1. temperatureunder reflux for total of 6 days
  2. customThe ethanol was removed
  3. additionthe reaction mixture was diluted with 100 mL ice water
  4. extractionextracted twice with 100 mL diethyl ether
  5. customA white precipitate formed
  6. filtrationwas filtered through a membrane
  7. filtrationfilter
  8. customThe aqueous layer from the filtrate was separated
  9. extractionextracted once with 100 mL ethyl acetate
  10. dry with materialdried with Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customThe crude product (2.54 g, yellow viscous oil) was purified over silica chromatography
  14. washeluting with a gradient
  15. customformed from heptane and ethyl acetate
  16. customto yield
  17. customafter evaporation of the product
  18. additioncontaining fractions 1.89 g (38%) of the title compound as off-white solid

Sources & evidence

ORD record
ord-cce90994544d462eb136b3cca075c08a
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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