Hydrochloric Acid → HCID 178521150, compound

HRID 469491Notes

Reaction equation

HRID 469491 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C([O:18][C:19]1[N:24]=[CH:23][C:22]([CH:25]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:26]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:27])=[CH:21][CH:20]=1)C1C=CC=CC=1.Cl>CCOC(C)=O.[Pd]>[Cl-:1].[OH:18][C:19]1[N:24]=[CH:23][C:22]([CH:25]([NH:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:26]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N+:31]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:32][CH2:33]3)[CH2:30]2)=[O:27])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 107572-ChloroacetophenoneHCID 58556981(R)-quinuclidin-3-yl 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetate

Product 1

HCID 178521150HCID 178521150, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (29.3 mg, 0.12 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetate (C53) (84 mg, 0.19 mmol, mixture of diastereomers) in EtOAc (4 ml). The reaction was stirred at room temperature overnight, and then a catalytic amount of 10% Pd/C (about 10 mg) and 37% HCl (0.50 ml) were added, and the reaction was hydrogenated at 20 psi for 2 hours. Pd/C is removed by filtration, and the clear solution was evaporated to dryness. The crude was purified by preparative HPLC to obtain (3R)-3-(2-(6-hydroxypyridin-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (20.3 mg, 18% yield).

Workup

  1. waitthe reaction was hydrogenated at 20 psi for 2 hours
  2. customPd/C is removed by filtration
  3. customthe clear solution was evaporated to dryness
  4. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-96233c654e004297bfff94775f45850b
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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