HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2104084
Notes
Print preview

Reaction equation

HRID 2104084 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-DichloroethaneSolvent
HCID 6342
Acetonitrile
Solvent

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-e17347b5cbaf451698832f362909d351
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576210B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes