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

HRID 130591Notes

Reaction equation

HRID 130591 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 kg) 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-f0e09029faaf43348c06de6baa5239f7
Source dataset
uspto-grants-2008_06
Patent number
US07381828B2

Reaction notes

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