Ethyl Acetate → HCID 66661149, compound

HRID 1019702Notes

Reaction equation

HRID 1019702 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6]([CH:8]=[C:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)=[O:7])#[N:2].[CH2:22]([Mg]Br)[CH3:23].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1.CCOCC>[C:1]([CH2:3][CH2:4][O:5][C:6]([CH2:8][C:9]1([CH2:22][CH3:23])[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 66660798HCID 66660798, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 66661149HCID 66661149, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.00 g (6.79 mmol) of tert-butyl 4-(cyanoethoxycarbonylmethylene)piperidine-1-carboxylate (WO 2006/001 752) in 33 mL of tetrahydrofuran are added dropwise, at −5° C. under argon, 4.53 mL (13.59 mmol) of a 3M solution of ethylmagnesium bromide in ether. The reaction medium is then stirred at room temperature for 12 hours. Ethyl acetate is added and the medium is cooled in a bath of ice/water, followed by addition of saturated ammonium chloride solution. The aqueous phase is separated out and extracted three times with ethyl acetate, the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel, eluting with a 95/5 mixture of cyclohexane and ethyl acetate to give 1.63 g of pure product in the form of a white powder.

Workup

  1. customThe aqueous phase is separated out
  2. extractionextracted three times with ethyl acetate
  3. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluting with a 95/5 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-6d45ed48414041f48a69c1b8822f389c
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

Loading…