Diethyl Ether → (3R)-3-(2-Hydroxy-2,2-dithien-2-ylacetoxy)-1-methyl-1-(3-thien-2-ylpropyl)pyrrolidinium bromide

HRID 458884Notes

Reaction equation

HRID 458884 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15](=[O:28])[C:16]([OH:27])([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[CH2:10]1.C[Br:30].[CH3:31]COCC>C(#N)C.C(Cl)(Cl)Cl>[Br-:30].[OH:27][C:16]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:15]([O:14][C@@H:11]1[CH2:12][CH2:13][N+:9]([CH3:31])([CH2:8][CH2:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH2:10]1)=[O:28]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6323Methyl BromideHCID 10048521HCID 10048521, compound2×

Product 1

HCID 69479721(3R)-3-(2-Hydroxy-2,2-dithien-2-ylacetoxy)-1-methyl-1-(3-thien-2-ylpropyl)pyrrolidinium bromide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent2×

Procedure

0.3 g (0.00069 mol) of 2-Hydroxy-2,2-dithien-2-ylacetic acid (3R)-1-(3-thien-2-ylpropyl)pyrrolidin-3-yl ester (Intermediate 1-3) were dissolved in 4 ml of acetonitrile and 6 ml of CHCl3. To this solution 3.45 ml (0.00345 mol) of a 1 M solution of methyl bromide in acetonitrile were added. After stirring the mixture at room temperature under N2 atmosphere during 24 h, the solvents were evaporated. Ether was added to the residue and the mixture stirred to obtain a solid. This solid was treated with ether several times, filtered and washed with ether. The yield was 0.34 g (93.2%) of the title compound as a mixture of two stereoisomers.

Workup

  1. customthe solvents were evaporated
  2. additionEther was added to the residue
  3. stirringthe mixture stirred
  4. customto obtain a solid
  5. filtrationfiltered
  6. washwashed with ether
  7. additionThe yield was 0.34 g (93.2%) of the title compound as a mixture of two stereoisomers

Sources & evidence

ORD record
ord-14e2fe93548a4fa9af636063bc496cac
Source dataset
uspto-grants-2007_03
Patent number
US07192978B2

Reaction notes

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