Hydrochloric Acid → HCID 59178494, compound

HRID 1691662Notes

Reaction equation

HRID 1691662 reaction equation
[C:1]([CH:3]([CH:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][C:10](OC)=[O:11])[C:4]([O:6][CH3:7])=[O:5])#[N:2].[BH4-].[Na+].Cl>CO.[Co](Cl)Cl>[O:11]=[C:10]1[NH:2][CH2:1][C@H:3]([C:4]([O:6][CH3:7])=[O:5])[C@@H:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59178512Dimethyl 2-cyano-3-phenylpentanedioate

Product 1

HCID 59178494HCID 59178494, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Procedure

To 1.0 L of a solution of 20.0 g of dimethyl 2-cyano-3-phenylpentanedioate and 36.4 g of cobalt chloride (TI) hexahydrate in methanol was added carefully 17.4 g of sodium borohydride under ice-cooling. After stirring at room temperature for 30 minutes, 1 M hydrochloric acid (1.0 L) was added thereto, followed by further stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure to a half amount thereof, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 3.84 g of methyl rel-(3R,4S)-6-oxo-4-phenylpiperidine-3-carboxylate as a white solid.

Workup

  1. temperaturecooling
  2. stirringby further stirring at room temperature for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure to a half amount
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-58515ada0f214e1c8af74475bf7d4965
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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