Ethanol heptane → HCID 68500325, compound

HRID 1963562Notes

Reaction equation

HRID 1963562 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][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][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]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][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]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=3)[CH2:8]2)[O:4][NH:3]1

Participants

5

Reactant 2

HCID 22502148Ethanol heptaneHCID 68500325HCID 68500325, compound

Product 2

HCID 66734963HCID 66734963, compoundYield 38.5%HCID 68500325HCID 68500325, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (205 mg, 0.53 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak IC (250×20), 5 μm particle size, mobile phase: Heptane/EtOH/FA 90/10/0.1, flow rate 18 mL/min) to yield (2S,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (77 mg, 38.5%), chiral purity 99.3% ee, Optical rotation [α]D20=+34.6 (acetonitrile, c=1) and (2R,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (87 mg, 43.5%), chiral purity 99.9% ee, Optical rotation [α]D20−30.2 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-e13b720e940d48208143b8fdd17d8e1c
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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