Phenacyl bromide → (R)-1-(2-oxo-2-phenylethyl)-3-((R)-3-phenyl-2-(phenylamino)propanoyloxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 77032Notes

Reaction equation

HRID 77032 reaction equation
[C:1]1([CH2:7][C@@H:8]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]>>[Br-:27].[O:30]=[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:28][N+:14]12[CH2:15][CH2:16][CH:17]([CH2:18][CH2:19]1)[C@@H:12]([O:11][C:9](=[O:10])[C@H:8]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:13]2

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 59401104HCID 59401104, compound

Product 1

HCID 46841669(R)-1-(2-oxo-2-phenylethyl)-3-((R)-3-phenyl-2-(phenylamino)propanoyloxy)-1-azoniabicyclo[2.2.2]octane bromideYield 98.1%

Procedure

To a solution of (R)-((R)-quinuclidin-3-yl) 3-phenyl-2-(phenylamino)propanoate (Diastereoisomer 1 of C22) (50.0 mg, 0.14 mmol), is added 2-bromo-1-phenylethanone (28.4 mg, 0.14 mmol) and the mixture reacted in a closed vessel under MW irradiation for 1 hour at 100° C. (LC-MS monitoring: complete conversion). Solvent is removed under reduced pressure and residue is triturated with EtOAc to obtain the title compound as a white solid (75.5 mg, 98% yield, bromide salt, single diastereoisomer).

Workup

  1. customthe mixture reacted in a closed vessel under MW irradiation for 1 hour at 100° C. (LC-MS monitoring: complete conversion)
  2. customSolvent is removed under reduced pressure and residue
  3. customis triturated with EtOAc

Sources & evidence

ORD record
ord-64227723a1e84f66b9faab31d58f2fd0
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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