HCID 131730439, compound → HCID 66735004, compound

HRID 1963496Notes

Reaction equation

HRID 1963496 reaction equation
[CH:1]1([C@H:7]2[CH2:12][C@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2[C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCO>[CH:1]1([C@@H:7]2[CH2:12][C@@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2[C:19]([O:21][CH3:22])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 131730439HCID 131730439, compound

Product 1

HCID 66735004HCID 66735004, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans-methyl 2-cyclohexyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (212 mg, 0.69 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×20), 5 μm particle size, mobile phase: EtOH, flow rate 12 mL/min) to yield (2S,4S)-methyl 2-cyclohexyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (79 mg, 37%), Chiral purity 99.3% ee. Optical rotation [α]D20=+5.1 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-150cc9cb13a441cfbbd296de6f0fd782
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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