HCID 131730436, compound → HCID 66734876, compound

HRID 1963490Notes

Reaction equation

HRID 1963490 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]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]2)[O:4][NH:3]1>CCCCCCC.CCO>[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]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]2)[O:4][NH:3]1

Participants

3

Reactant 1

HCID 131730436HCID 131730436, compound

Product 1

HCID 66734876HCID 66734876, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 22502148Ethanol heptaneSolvent

Procedure

Racemic trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-phenylpiperidine-1-carboxylate (772 mg, 2.55 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 75/25, flow rate 15 mL/min) to yield (2S,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-phenylpiperidine-1-carboxylate (249 mg, 32%). Optical rotation [α]D20=+23.0 (acetonitrile, c=1), Chiral purity 99.7% ee.

Sources & evidence

ORD record
ord-46b9929ca02c43dca08703713eb8ff2d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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