Ethanol heptane → HCID 66734914, compound

HRID 1963573Notes

Reaction equation

HRID 1963573 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]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[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:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:25])[F:26])[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:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:25])[F:26])[CH2:8]2)[O:4][NH:3]1

Participants

5

Reactant 2

HCID 22502148Ethanol heptaneHCID 68504952(2R,4S)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(2-(trifluoromethyl)benzyl)piperidine-1-carboxylate

Product 2

HCID 66734914HCID 66734914, compoundYield 48%HCID 68504952(2R,4S)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(2-(trifluoromethyl)benzyl)piperidine-1-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(2-(trifluoromethyl)benzyl)piperidine-1-carboxylate (1.30 g, 3.39 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×20), 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-(2-(trifluoromethyl)benzyl)piperidine-1-carboxylate (597 mg, 46%), Chiral purity 99.6% ee, Optical rotation [α]D20=−4.0 (acetonitrile, c=1) and (2S,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(2-(trifluoromethyl)benzyl)piperidine-1-carboxylate (624 mg, 48%), Chiral purity 99.8% ee, Optical rotation [α]D20=+6.1 (acetonitrile, c=1).

Sources & evidence

ORD record
ord-8fcd4bc7d8f940f39e07c07d32111dab
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…