(3S,3aR,6aR)-5,5-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole → (3R,3aS,6aS)-5,5-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole

HRID 444800

Reaction equation

HRID 444800 reaction equation
[F:1][C:2]1([F:18])[CH2:17][C@@H:5]2[C@:6]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])([CH3:9])[NH:7][O:8][C@@H:4]2[CH2:3]1>CCCCCCC.C(O)C>[F:18][C:2]1([F:1])[CH2:17][C@H:5]2[C@@:6]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])([CH3:9])[NH:7][O:8][C@H:4]2[CH2:3]1

Participants

3

Reactant 1

HCID 86678552(3S,3aR,6aR)-5,5-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole

Product 1

HCID 86678551(3R,3aS,6aS)-5,5-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole

Reagents, catalysts & solvents 1

HCID 22502148Ethanol heptaneSolvent

Procedure

Intermediate IX-1: The racemate of (3S,3aR,6aR)-5,5-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole was resolved on a chiral high-performance liquid chromatography (HPLC) column (Chiralpak AD) using n-heptane/ethanol (85:15) to give (3R,3aS,6aS)-5,5-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole as the faster eluting enantiomer and the desired (3S,3aR,6aR)-5,5-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole as the slower eluting enantiomer. MS: m/z=258.2 [M+H]+.

Sources & evidence

ORD record
ord-5b81d7fc022f4c268535d27a448701c5
Source dataset
uspto-grants-2013_07
Patent number
US08476264B2

Linked notes

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