Benzene, (3-bromopropoxy)- → Aclidinium Bromide

HRID 1666964Notes

Reaction equation

HRID 1666964 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:23])[C:11]([OH:22])([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH2:2]2.[O:24]([CH2:31][CH2:32][CH2:33][Br:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC#N.C(Cl)(Cl)Cl>[Br-:34].[OH:22][C:11]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:10]([O:9][C@@H:3]1[CH:4]2[CH2:7][CH2:8][N+:1]([CH2:33][CH2:32][CH2:31][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH2:6][CH2:5]2)[CH2:2]1)=[O:23]

Participants

5

Reactant 2

HCID 68522Benzene, (3-bromopropoxy)-HCID 44232927(R)-Quinuclidin-3-yl 2-hydroxy-2,2-di(thiophen-2-yl)acetate

Product 1

HCID 11519741Aclidinium BromideYield 90%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

0.6 mmol of 2-hydroxy-2,2-dithien-2-ylacetic acid 1-azabicyclo[2.2.2]oct-3(R)yl ester are suspended in 4 ml of CH3CN and 6 ml of CHCl3. 0.48 ml of 3-phenoxypropyl bromide were added to the resulting suspension and the mixture was stirred for 72 h at room temperature in an inert atmosphere. The solvents were subsequently evaporated to yield (90%) of 3(R)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide. The product is isolated by filtration at room temperature and the level of 3-phenoxypropyl bromide is determined to be 117 ppm.

Workup

  1. customThe solvents were subsequently evaporated

Sources & evidence

ORD record
ord-a6fe5cd3973e4a57ac27ed7cd670dca0
Source dataset
uspto-grants-2011_10
Patent number
US08044205B2

Reaction notes

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