Cesium carbonate → HCID 71205443, compound

HRID 2280857Notes

Reaction equation

HRID 2280857 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].[NH:18]1[CH2:25]CC[C@H:19]1[C:20](O)=[O:21]>CS(C)=O.CC(=O)OCC.O.[Cu]I>[OH:21][CH:20]1[CH2:19][N:18]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:25]1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 69258Methyl 3-iodobenzoateHCID 145742L-Proline

Product 1

HCID 71205443HCID 71205443, compoundYield 164.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-iodobenzoate (4.5 g, 17.2 mmol) in DMSO (30 mL) was added 3-azetidin-3-ol hydrogen chloride salt (1.3 g, 11.8 mmol), Cs2CO3 (9.5 g, 29.2 mmol), CuI (446 mg, 2.3 mmol) and L-proline (540 mg, 4.7 mmol) and then the mixture was heated at 90° C. for 18 h under argon atmosphere. The solution was diluted with EA and water and the organic layer was washed with brine three times, concentrated under reduced pressure and purified by CC (PE/EA=2:1) to give compound 3a (1.6 g, 66%) as a yellow solid.

Workup

  1. washthe organic layer was washed with brine three times
  2. concentrationconcentrated under reduced pressure
  3. custompurified by CC (PE/EA=2:1)

Sources & evidence

ORD record
ord-02c7363b874e4a10aa1f3f2ef7c8d3df
Source dataset
uspto-grants-2015_09
Patent number
US09139539B2

Reaction notes

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