Ethanol heptane → HCID 68504120, compound

HRID 1963648Notes

Reaction equation

HRID 1963648 reaction equation
[O:1]=[C:2]1[CH:6]=[C:5]([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[C@@H:9]([CH2:17][C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[CH:19]=3)[CH2:8]2)[O:4][NH:3]1.CCCCCCC.CCO>C(#N)C>[O:1]=[C:2]1[CH:6]=[C:5]([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[C@@H:9]([CH2:17][C:18]3[CH:19]=[C:20]([F:26])[C:21]([F:25])=[C:22]([F:24])[CH:23]=3)[CH2:8]2)[O:4][NH:3]1.[O:1]=[C:2]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[C@H:9]([CH2:17][C:18]3[CH:19]=[C:20]([F:26])[C:21]([F:25])=[C:22]([F:24])[CH:23]=3)[CH2:8]2)[O:4][NH:3]1

Participants

5

Reactant 2

HCID 22502148Ethanol heptaneHCID 68501674HCID 68501674, compound

Product 2

HCID 68501674HCID 68501674, compoundYield 43%HCID 68504120HCID 68504120, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3,4,5-trifluorobenzyl)piperidine-1-carboxylate (1.354 g, 3.68 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20 mm), 5 μm particle size, mobile phase: Heptane/EtOH/FA 80/20/0.1, flow rate 18 mL/min) to yield (2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3,4,5-trifluorobenzyl)piperidine-1-carboxylate (584 mg, 43%), Chiral purity 99.3% ee, Optical rotation [α]D20=+13.0 (acetonitrile, c=1.0) and (2S,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3,4,5-trifluorobenzyl)piperidine-1-carboxylate (598 mg, 44%), Chiral purity 99.2% ee, Optical rotation [α]D20=−12.5 (acetonitrile, c=1.0)

Sources & evidence

ORD record
ord-48f2393ecd584256be487d9304d25494
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…