Hydrochloric Acid → ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionate

HRID 2192924Notes

Reaction equation

HRID 2192924 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:16](=[CH:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[BH4-].[Na+].Cl.O>C(O)C.C1COCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:16]([CH2:22][CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:11])=[O:12])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 68670876ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

Product 1

HCID 59571058ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionateYield 107.1%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (2.62 g) in ethanol (24 mL) and THF (12 mL) was added nickel(II) chloride hexahydrate (154 mg) under ice-cooling. Subsequently, sodium borohydride (489 mg) was added thereto under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture were added 1 M hydrochloric acid and water under ice-cooling. The resulting black solid was removed by filtration through Celite and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration, ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionate (2.82 g) was obtained as a colorless oily substance.

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. temperaturecooling
  4. customThe resulting black solid was removed by filtration through Celite
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationAfter concentration

Sources & evidence

ORD record
ord-014e0ca25c1f46b5bba477d6458526fa
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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