Heptane → HCID 90021485, compound

HRID 710192Notes

Reaction equation

HRID 710192 reaction equation
[F:1][C:2]1([F:18])[CH:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])([CH3:10])[NH:8][O:9][CH:5]2[CH2:4][CH2:3]1.CCCCCCC>C(O)C>[F:18][C:2]1([F:1])[C@H:6]2[C@@:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])([CH3:10])[NH:8][O:9][C@H:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 8900HeptaneHCID 90021527HCID 90021527, compound

Product 1

HCID 90021485HCID 90021485, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediates IX-1: The rac-(3S,3aR,6aR)-4,4-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole was resolved by high-performance liquid chromatography (HPLC) on a chiral phase (Chiralpak AD) using a 90:10-mixture of n-heptane and ethanol as the eluent to give the (3R,3aS,6aS)-4,4-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole (intermediate IXb-1) as the faster eluting enantiomer (30% yield) and the desired (3S,3aR,6aR)-4,4-difluoro-3-(2-fluoro-phenyl)-3-methyl-hexahydro-cyclopenta[d]isoxazole (intermediate IXa-1) as the slower eluting enantiomer (27% yield) both as light yellow oils.

Sources & evidence

ORD record
ord-54a98e7c65344de7894806a3c711ff64
Source dataset
uspto-grants-2015_11
Patent number
US09181232B2

Reaction notes

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