Ethanol heptane → HCID 68499998, compound

HRID 1963634Notes

Reaction equation

HRID 1963634 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].CCCCCCC.CCO>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=1)[CH2:5][C@@H:6]1[CH2:11][C@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 22502148Ethanol heptaneHCID 68499998HCID 68499998, compound

Product 2

HCID 66734567HCID 66734567, compoundYield 45.9%HCID 68499998HCID 68499998, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-Methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (1.47 g, 3.66 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 90/10, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (703 mg, 47.8%), Chiral purity 99.3% ee, Optical rotation [α]D20=+5.5 (acetonitrile, c=1) and (2S,4R)-methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (675 mg, 45.9%), Chiral purity 99.7% ee, Optical rotation [α]D20=−5.1 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-bb4a5c3ec233495d97f8f89f3bbcd913
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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