Diethyl Ether → 3-(2-Cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1-(ethoxycarbonylmethyl)-1-methylpyrrolidinium bromide

HRID 748614Notes

Reaction equation

HRID 748614 reaction equation
[CH:1]1([C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[C:7]([O:9][CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(OCC)C>C(#N)C.C(Cl)CCl>[Br-:23].[CH:1]1([C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[C:7]([O:9][CH:10]2[CH2:14][CH2:13][N+:12]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])([CH3:15])[CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 25727N-Methyl-3-pyrrolidinyl Cyclopentylmandelate

Product 1

HCID 167228483-(2-Cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1-(ethoxycarbonylmethyl)-1-methylpyrrolidinium bromide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6342AcetonitrileSolvent

Procedure

To compound 4 (0.369 g, 1.22 mmol) in 10 ml of dry acetonitrile, ethyl bromoacetate (0.377 g, 2.25 mmol) was added at room temperature. The mixture was stirred for 2 h. Evaporation of acetonitrile gave a crude product. The crude product was dissolved in a small volume of ethylene chloride and then poured into 50 ml of dry ethyl ether to precipitate. This procedure was repeated three times to obtain Compound (b) as pure product (0.45 g, 79%). White powder, m.p.: 192-194° C.

Workup

  1. customEvaporation of acetonitrile
  2. customgave a crude product
  3. customto precipitate

Sources & evidence

ORD record
ord-15e110c1325a4d29b6cec589fefd5b51
Source dataset
uspto-grants-2008_07
Patent number
US07399861B2

Reaction notes

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