HCID 18365356, compound → HCID 67567050, compound

HRID 380552Notes

Reaction equation

HRID 380552 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[Cl:23][C:21]1[CH:20]=[CH:19][C:17]2[N:18]=[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[S:15][C:16]=2[CH:22]=1

Participants

5

Reactant 2

HCID 18365356HCID 18365356, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67567050HCID 67567050, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.939 gm (2.7 mMol) 1-tert-butoxycarbonyl-4-(6-chlorobenzothiazol-2-yl)-1,2,3,6-tetrahydropyridine and a catalytic amount of platinum oxide in 20 mL methanol was stirred at room temperature under about 1 atmosphere of hydrogen for about 3 hours. The reaction mixture was concentrated under reduced pressure, the residue dissolved in a minimal volume of ethyl acetate, and the mixture filtered through a bed of flash silica gel, eluting with 1:1 hexane:ethyl acetate. The filtrate was concentrated under reduced pressure to provide 0.663 gm (70%) of the desired compound as a light tan oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in a minimal volume of ethyl acetate
  3. filtrationthe mixture filtered through a bed of flash silica gel
  4. washeluting with 1:1 hexane
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3fc36b84efb348ba97dcb8156db3e388
Source dataset
uspto-grants-2001_10
Patent number
US06303627B1

Reaction notes

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