Ethanol → (2S,4S)-Methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate

HRID 1963542Notes

Reaction equation

HRID 1963542 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][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])=[CH:4][CH:3]=1.CCO.C(#N)C>C(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][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])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6342AcetonitrileHCID 131730459trans-Methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 66739000(2S,4S)-Methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylateYield 30.3%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Trans-methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.268 g, 0.8 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×30), 5 μm particle size, mobile phase: 10% EtOH in CO2 (175 bar), flow rate 150 mL/min) to yield (2S,4S)-methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (81 mg, 30%), Chiral purity 99.8% ee, Optical rotation [α]D20=+29.3 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-4e65de0dc4c14ba18a7ead270b55f7c1
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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