Cesium carbonate → (2R)-1-[2-(4-iodophenoxy)ethyl]-2-methylpyrrolidine

HRID 1364224Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1>C(#N)C>[I:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][N:3]2[CH2:4][CH2:5][CH2:6][C@H:2]2[CH3:1])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of (2R)-2-methylpyrrolidine (0.60 g) and cesium carbonate (1.2 g) in acetonitrile (3 mL), 1-(2-chloroethoxy)-4-iodobenzene obtained in Example 60-(1) (0.87 g) was added and the mixture was heated to 100° C., at which it was stirred for 9 hours. The reaction mixture was cooled to room temperature and filtered to remove insoluble materials, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=9:1 to 1:1) to give the titled compound (0.80 g, 78%) as a colorless oil.

Workup

additionwas added
temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
customto remove insoluble materials
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record: ord-bf91afe45685498a8312cc2522618b57
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888354B2

Reaction notes

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