Isopropanol heptane → (2R,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate

HRID 1963536Notes

Reaction equation

HRID 1963536 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][C@H:5]1[CH2:10][C@H:9]([C:11]2[O:15][NH:14][C:13](=[O:16])[CH:12]=2)[CH2:8][CH2:7][N:6]1[C:17]([O:19][CH3:20])=[O:18].CCCCCCC.CC(O)C>C(#N)C>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][C@@H:5]1[CH2:10][C@@H:9]([C:11]2[O:15][NH:14][C:13](=[O:16])[CH:12]=2)[CH2:8][CH2:7][N:6]1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 21225753Isopropanol heptaneHCID 131730456trans-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 66732587(2R,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trans-methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (194 mg, 0.63 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak IC (250×20), 5 μm particle size, mobile phase: Heptane/IPA 85/15, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (83 mg, 43%), Chiral purity 99.3% ee, Optical rotation [α]D20=−12.3 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-cc8ad5f866b84dacb3e4170160ab15b1
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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