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

HRID 1831484Notes

Reaction equation

HRID 1831484 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-iopropyl-5-methylcyclohexyl trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylate.

Sources & evidence

ORD record
ord-8c0683bfcab14c88a716b9eec72469d5
Source dataset
uspto-grants-2006_06
Patent number
US07067663B2

Reaction notes

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