1-Methyl-1,4-cyclohexadiene → (R)-quinuclidin-3-yl((S)-phenyl(3-(piperidin-4-ylmethoxy)phenyl)methyl)carbamate

HRID 874834Notes

Reaction equation

HRID 874834 reaction equation
[C:1]1([C@H:7]([NH:32][C:33]([O:35][C@@H:36]2[CH:41]3[CH2:42][CH2:43][N:38]([CH2:39][CH2:40]3)[CH2:37]2)=[O:34])[C:8]2[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=2)[O:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16](C(OCC3C=CC=CC=3)=O)[CH2:15][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1CC=CCC=1>C(O)C.[Pd]>[N:38]12[CH2:39][CH2:40][CH:41]([CH2:42][CH2:43]1)[C@@H:36]([O:35][C:33](=[O:34])[NH:32][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[CH:31]=[CH:30][CH:29]=[C:10]([O:11][CH2:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[CH:9]=1)[CH2:37]2

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 90198097benzyl 4-((3-((5)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)-amino)methyl)phenoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 90210005(R)-quinuclidin-3-yl((S)-phenyl(3-(piperidin-4-ylmethoxy)phenyl)methyl)carbamateYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)-amino)methyl)phenoxy)methyl)piperidine-1-carboxylate (1.32 g, 2.26 mmol) in ethanol (100 mL) was added palladium on charcoal (0.66 g) and stirred at room temperature for 10 minutes. 1-Methyl-1,4-cyclohexadiene (1.27 mL, 11.3 mmol) was added and the reaction mixture heated to reflux. The reaction mixture was stirred under reflux for 1 hour. The reaction mixture was allowed to cool and the suspension filtered. The filtrate was evaporated at reduced pressure to afford the title compound (1.05 g, 100%).

Workup

  1. temperaturethe reaction mixture heated to reflux
  2. stirringThe reaction mixture was stirred
  3. temperatureunder reflux for 1 hour
  4. temperatureto cool
  5. filtrationthe suspension filtered
  6. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-77bbac0e13e0450b9ecb6b41af83b3ec
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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