Isopropanol heptane → HCID 66742254, compound

HRID 1963520Notes

Reaction equation

HRID 1963520 reaction equation
[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH:5]([CH2:8][C@H:9]2[CH2:14][C@@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH3:24])=[O:22])[CH2:4][CH2:3]1.CCCCCCC.CC(O)C>C(#N)C>[F:25][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([CH2:8][C@H:9]2[CH2:14][C@@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH3:24])=[O:22])[CH2:4][CH2:3]1.[F:25][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([CH2:8][C@@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH3:24])=[O:22])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 21225753Isopropanol heptaneHCID 66742254HCID 66742254, compound

Product 2

HCID 66732723HCID 66732723, compoundYield 47%HCID 66742254HCID 66742254, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-methyl 2-((4,4-difluorocyclohexyl)methyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.6 g, 4.46 mmol) was subjected to chiral preparative HPLC (Column: CelluCoat (250×20), 5 μm particle size, mobile phase: Heptane/IPA 80/20, flow rate 18 mL/min) to yield (2S,4S)-methyl 2-((4,4-difluorocyclohexyl)methyl)-4-(3-oxo-2,3-dihydro-isoxazol-5-yl)piperidine-1-carboxylate (787 mg, 49%), Chiral purity 99.8% ee, Optical rotation [α]D20=+28.8 (acetonitrile, c=1) and (2R,4R)-methyl 2-((4,4-difluorocyclohexyl)-methyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (752 mg, 47%) Chiral purity 99.9% ee, Optical rotation [α]D20=−30.2 (acetonitrile, c=1).

Sources & evidence

ORD record
ord-a558c06a93d84b8c94bc2d9f49e2113f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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