1-Benzyloxycarbonyl-4-(2-fluoropyrid-3-yl)-1,2,3,6-tetrahydropyridine → 1-Benzyloxycarbonyl-4-(2-fluoropyrid-3-yl)piperidine

HRID 2256067Notes

Reaction equation

HRID 2256067 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pt]=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 190291271-Benzyloxycarbonyl-4-(2-fluoropyrid-3-yl)-1,2,3,6-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 190291611-Benzyloxycarbonyl-4-(2-fluoropyrid-3-yl)piperidineYield 97.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(2-fluoropyrid-3-yl)-1,2,3,6-tetrahydropyridine (2.04 g) in 50 mL of ethanol was treated with platinum oxide (0.22 g) and the mixture was hydrogenated (3.4 bar hydrogen pressure) for 16 hours. At the end of this period, the reaction mixture was filtered through a pad of diatomaceous earth and the filtrate was evaporated to afford the named material as a white solid (2.0 g); MS: 315; NMR: 1.6 (br, 2), 1.8-1.9 (d, J=14, 2), 2.8-3.1 (m, 3), 4.3 (b, 2), 5.1 (s, 2), 7.1-7.2 (m, 1), 7.2-7.4 (m, 5), 7.6 (m, 1), 8.1 (m, 1).

Workup

  1. customfor 16 hours
  2. filtrationAt the end of this period, the reaction mixture was filtered through a pad of diatomaceous earth
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c87e0a9c6155458cbbdbe3e50f800413
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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