Benzyl chloroformate → HCID 15117236, compound

HRID 1029627Notes

Reaction equation

HRID 1029627 reaction equation
[C:1]([C:4]1[CH2:5][CH2:6][N:7](CC2C=CC=CC=2)[CH2:8][CH:9]=1)(=[O:3])[CH3:2].[CH2:17]([O:24][C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH2:9][CH2:8][N:7]([C:25]([O:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[CH2:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 13876719HCID 13876719, compound

Product 1

HCID 15117236HCID 15117236, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-acetyl-1-benzyl-1,2,3,6-tetrahydropyridine (9.63 g) and benzyloxycarbonyl chloride (9.06 ml) in toluene was heated at 85° C. for 8 hours. After the solvent was removed in vacuo, the residual solution was dissolved in ethyl acetate (100 ml), washed with saturated aqueous sodium hydrogen carbonate (100 ml×3) and brine (100 ml) successively. The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo to give an oil, which was chromatographed on silica gel (500 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give 4-acetyl-1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine (10.2 g).

Workup

  1. customAfter the solvent was removed in vacuo
  2. dissolutionthe residual solution was dissolved in ethyl acetate (100 ml)
  3. washwashed with saturated aqueous sodium hydrogen carbonate (100 ml×3) and brine (100 ml) successively
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil, which
  8. customwas chromatographed on silica gel (500 ml)
  9. washeluting with a mixture of hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-442e5ebee83b464c84d9fd3466305308
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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