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

HRID 2104083Notes

Reaction equation

HRID 2104083 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, 2dd, 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-e866ca75e62943a19375d4b3f2554f93
Source dataset
uspto-grants-2009_08
Patent number
US07576210B2

Reaction notes

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