HCID 19992023, compound → HCID 19991999, compound

HRID 345293Notes

Reaction equation

HRID 345293 reaction equation
[CH2:1]([C:4]12[CH2:11][O:10][C:7]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14](C(OCC4C=CC=CC=4)=O)[CH2:13]3)([O:8][CH2:9]1)[O:6][CH2:5]2)[CH2:2][CH3:3]>O1CCCC1.[Pd]>[CH2:1]([C:4]12[CH2:5][O:6][C:7]([CH:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)([O:8][CH2:9]1)[O:10][CH2:11]2)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 19992023HCID 19992023, compound

Product 1

HCID 19991999HCID 19991999, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 3-(4-n-propyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)piperidine-1-carboxylate (7.0 g.) in dry tetrahydrofuran (100 ml) under nitrogen, was added 5% palladium on carbon (0.63 g.) and the system was hydrogenated at atmospheric pressure. When the theoretical volume uptake (450 ml) had been achieved the system was purged with nitrogen and the mixture was filtered through celite. The solution was evaporated in vacuo. The resulting solid was recrystallised from hexane. 3-(4-n-Propyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)piperidine (3.3 g.) was obtained as colourless crystals.

Workup

  1. customwas purged with nitrogen
  2. filtrationthe mixture was filtered through celite
  3. customThe solution was evaporated in vacuo
  4. customThe resulting solid was recrystallised from hexane

Sources & evidence

ORD record
ord-ef3cc80f72c84cb1986765ed73f08121
Source dataset
uspto-grants-1991_10
Patent number
US05057504

Reaction notes

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