Sodium methanesulfinate → [1-(5-Methanesulfonyl-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

HRID 2172968Notes

Reaction equation

HRID 2172968 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1([C:11]2[O:12][C:13](I)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][S:19]([O-:21])=[O:20].[Na+].COC(=O)CCS([O-])=O.[Na+]>[Cu]I>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1([C:11]2[O:12][C:13]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 2733271Sodium methanesulfinateHCID 23665669Sodium 1-Methyl 3-SulfinopropionateHCID 67115732[1-(5-Iodo-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Product 1

HCID 68377483[1-(5-Methanesulfonyl-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

[1-(5-Methanesulfonyl-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester is prepared from [1-(5-iodo-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.500 g, 1.43 mmol) according to the copper (I) iodide-mediated coupling procedure described in Example 19; however, sodium methanesulfinate is used as coupling partner instead of sodium 3-methoxy-3-oxopropane-1-sulfinate.

Sources & evidence

ORD record
ord-500e57a77e914bf281e7f0756adb24a5
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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