t-Butyl (1-t-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)phenylcarbamate → t-Butyl (1-t-Butoxycarbonylpiperidin-4-yl)phenylcarbamate

HRID 1419569Notes

Reaction equation

HRID 1419569 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([N:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 53951936t-Butyl (1-t-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)phenylcarbamate

Product 1

HCID 54392086t-Butyl (1-t-Butoxycarbonylpiperidin-4-yl)phenylcarbamateYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

t-Butyl (1-t-butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)phenylcarbamate (2.5 g) was dissolved in ethanol, palladium on carbon (10%) was added and the mixture was shaken under hydrogen (50 psi.) for 3 h. The mixture was filtered through Hyflo and the solvent was evaporated under reduced pressure. The residue was purified by MPLC on silica gel, eluting with EtOAc/Hexane (5:95) to give the title compound as a clear oil (2.44 g), δH (CDCl3) 1.51 (9H, s), 1.55 (9H, s), 1.69 (2H, m), 1.79 (2H, m), 2.77 (3H, m), 4.24 (2H, m), 6.18 (1H, br s), 7.12-7.18 (3H, m), 7.52 (1H, m). m/e (CI+) 377 (MH+).

Workup

  1. filtrationThe mixture was filtered through Hyflo
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by MPLC on silica gel
  4. washeluting with EtOAc/Hexane (5:95)

Sources & evidence

ORD record
ord-557fc6d3aded4f40ad1e18d62f58044e
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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