Isopropanol heptane → HCID 66734693, compound

HRID 1963434Notes

Reaction equation

HRID 1963434 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CCCCCCC.CC(O)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([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])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:1][C:2]1[CH:3]=[C:4]([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])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 21225753Isopropanol heptaneHCID 68502101HCID 68502101, compound

Product 2

HCID 66734693HCID 66734693, compoundYield 50%HCID 68502101HCID 68502101, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-methyl 2-(3,5-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (2.000 g, 5.4 mmol) was subjected to chiral preparative HPLC (Column: CelluCoat (250×50 mm), 10 μm particle size, mobile phase: Heptane/EtOH 70/30, flow rate 120 mL/min) to yield (2R,4S)-methyl 2-(3,5-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.05 g, 50%), Chiral purity 99.6% ee, Optical rotation [α]D20=+67.1 (acetonitrile, c=1.0), and (2S,4R)-methyl 2-(3,5-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.06 g, 50%), Chiral purity 97.6% ee, Optical rotation [α]D20=−58.4 (acetonitrile, c=1.0).

Sources & evidence

ORD record
ord-5369b78edc904e1ab01f0e753bdb17d7
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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