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

HRID 1045250Notes

Reaction equation

HRID 1045250 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][CH3:28])=[O:26].C(OCC)C>C(#N)C.C(Cl)Cl>[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][CH3:28])=[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 25727N-Methyl-3-pyrrolidinyl CyclopentylmandelateHCID 60984Methyl bromoacetate

Product 1

HCID 167228463-(2-Cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1-(methoxycarbonylmethyl)-1-methylpyrrolidinium bromide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To compound 4 (0.8235 g, 2.71 mmol) in 30 ml of dry acetonitrile, methyl bromoacetate (1.08 g, 7.06 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 methylene chloride and then poured into 100 ml of dry ethyl ether to precipitate. This procedure was repeated three times to obtain Compound (a) as pure product (0.9912 g, 80%). White powder, m.p.: 192-194° C. Analysis for C21H30BrNO5. Calcd: C, 55.27; H, 6.63; N, 3.07. Found: C, 55.11; H, 6.59; N, 3.03. 1H NMR (CDCl3, 500 MHz): 1.23-1.29, 1.31-1.37, 1.41-1.47, 1.53-1.67 [8H, m, (CH2)4], 2.18-2.23, 2.73-2.80, 4.04-4.16, 4.21-4.25 (6H, m, CH2NCH2CH2), 2.85 [1H, p, CHC(OH)], 3.57 (3H, s, NCH3), 3.80 (3H, s, CO2CH3), 4.66, 4.85 (2H, 2 dd, CH2CO2), 5.27 (1H, s, OH), 5.52 (1H, m, CO2CH), 7.25-7.28, 7.32-7.35, 7.57-7.59 (5H, m, Ph) ppm.

Workup

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

Sources & evidence

ORD record
ord-61eda554f093438cb44d00608e91bdb2
Source dataset
uspto-grants-2013_10
Patent number
US08568699B2

Reaction notes

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