Picolyl chloride → HCID 57425756, compound

HRID 1441236Notes

Reaction equation

HRID 1441236 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[C:1]([C:3]1([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2]

Participants

6

Reactant 3

HCID 23393Picolyl chlorideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 57425756HCID 57425756, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred suspension of tert-butyl 4-cyanopiperidine-1-carboxylate (500 mg; 2.38 mmol) and 2-(chloromethyl)pyridine (334 mg; 2.62 mmol) in toluene (3.6 ml) cooled in an ice bath was added a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene; 5.7 ml; 2.86 mmol) over 10 minutes. The reaction mixture was allowed to warm to ambient temperature with stirring for 1.5 hours. The reaction was poured into brine (25 ml) and extracted with EtOAc (3×30 ml). The combined organic extracts were washed with brine (30 ml), dried over MgSO4, filtered and evaporated to give a orange oil. The crude product was chromatographed on silica eluted with 50% EtOAc in isohexane to give the desired product a colourless oil. (375 mg)

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with EtOAc (3×30 ml)
  3. washThe combined organic extracts were washed with brine (30 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a orange oil
  8. customThe crude product was chromatographed on silica
  9. washeluted with 50% EtOAc in isohexane

Sources & evidence

ORD record
ord-90da2f6789d247e0a1d7b2a3332ec5d2
Source dataset
uspto-grants-2010_02
Patent number
US07655644B2

Reaction notes

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