HCID 86665860, compound → HCID 67607403, compound

HRID 1619577Notes

Reaction equation

HRID 1619577 reaction equation
[Br-].C([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N+:23](CC(=O)C4C=CC=CC=4)([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])=[CH:12][CH:11]=1)C1C=CC=CC=1>CO.[Pd]>[C:42]([O:41][C:39]([NH:38][C@@H:17]([CH2:16][C:13]1[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][CH:12]=1)[C:18]([O:20][C@@H:21]1[CH:26]2[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]2)[CH2:22]1)=[O:19])=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

4

Reactant 1

HCID 86665860HCID 86665860, compound

Product 1

HCID 67607403HCID 67607403, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-3-((S)-3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)-propanoyloxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (720 mg, 1.06 mmol) and 10% Pd/C (100 mg, 0.09 mmol) in MeOH (30 ml) was hydrogenated at 25 psi for 2 hours. The catalyst was removed by filtration, and the solvent was evaporated to dryness. The residue was dissolved in DCM and filtered through a SCX cartridge. The solution was evaporated to obtain (S)—((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate (260 mg, 62.9% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated to dryness
  3. dissolutionThe residue was dissolved in DCM
  4. filtrationfiltered through a SCX cartridge
  5. customThe solution was evaporated

Sources & evidence

ORD record
ord-dd4bbba6adf9443493b54c2bad7307aa
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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