Diisopropyl Ether → Fesoterodine fumarate

HRID 1484400Notes

Reaction equation

HRID 1484400 reaction equation
[CH3:1][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[O:5])[CH3:3].C(OC(C)C)(C)C.CC(C)=O.[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46]>>[CH3:3][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:21])[CH3:22])[CH:17]([CH3:18])[CH3:19])=[O:5])[CH3:1].[CH:43](/[C:42]([OH:49])=[O:48])=[CH:44]\[C:45]([OH:47])=[O:46]

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 6918558FesoterodineHCID 90135091HCID 90135091, compound

Product 1

HCID 9849808Fesoterodine fumarate

Procedure

A 7% solution of aqueous NaHCO3 (25 ml) was added to a suspension of Fesoterodine Hydrochloride monohydrate (5 g) in dichloromethane (50 ml) at 10-15° C. The resulting mixture was stirred at room temperature and the two phases were separated. The organic phase was evaporated under reduced pressure; acetone (10 ml) was added twice and evaporated under reduced pressure to afford a Fesoterodine base solution. The Fesoterodine base solution was added over an acetone/fumaric acid suspension (10 ml/1.25 g) at 15-20° C. Diisopropyl ether 5 ml was added at 10-15° C. and the suspension was stirred to allow crystallization for 1-2 h, then diisopropyl ether 5 ml was added and the suspension stirred for 1-2 h. Finally diisopropyl ether (30 ml) was added and the suspension stirred for another 1-2 h. The suspension was filtered off and the crystallized product was washed with acetone/diisopropyl ether (10 ml), to yield 5.1 g of the corresponding Fesoterodine Fumarate.

Workup

  1. customcrystallization for 1-2 h
  2. additiondiisopropyl ether 5 ml was added
  3. stirringthe suspension stirred for 1-2 h
  4. additionFinally diisopropyl ether (30 ml) was added
  5. stirringthe suspension stirred for another 1-2 h
  6. filtrationThe suspension was filtered off
  7. washthe crystallized product was washed with acetone/diisopropyl ether (10 ml)

Sources & evidence

ORD record
ord-9eb7df8f1d084cd7a71067f46de8f0bd
Source dataset
uspto-grants-2016_08
Patent number
US09422228B2

Reaction notes

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