Sodium Iodide → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl trans-2-(3,4-difluorophenyl)cyclopropanecarboxylate

HRID 2390761Notes

Reaction equation

HRID 2390761 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([O:13][C@@H:14]2[CH2:19][C@H:18]([CH3:20])[CH2:17][CH2:16][C@H:15]2[CH:21]([CH3:23])[CH3:22])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:24]S(C)(=O)=C.[I-].[Na+].[OH-].[Na+]>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:24][C@H:10]2[C:11]([O:13][C@@H:14]2[CH2:19][C@H:18]([CH3:20])[CH2:17][CH2:16][C@H:15]2[CH:21]([CH3:23])[CH3:22])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 6396768Dimethylsulfoxonium methylideHCID 10268077(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (E)-3-(3,4-difluorophenyl)-2-propenoate

Product 1

HCID 9859000(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl trans-2-(3,4-difluorophenyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl(E)-3-(3,4-difluorophenyl)-2-propenoate (approximately 8.6 kg) in dimethyl sulfoxide (approximately 27.9 kg) was added with stirring over 20 minutes to a mixture of dimethylsulfoxonium methylide (approximately 2.6 kg, prepared as described above), sodium iodide (approximately 4.2 kg), water (approximately 500 g) and sodium hydroxide (approximately 56 g) in dimethylsulfoxide (27.7 kg) at 25° C. The reaction mixture was stirred for a further 2 hours and 50 minutes at 25° C., then used directly for the preparation of (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylate.

Sources & evidence

ORD record
ord-5f19f3702eeb4e6d866705e8efb83301
Source dataset
uspto-grants-2012_09
Patent number
US08273879B2

Reaction notes

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