Isopropanol heptane → HCID 68500328, compound

HRID 1963622Notes

Reaction equation

HRID 1963622 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([F:25])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].CCCCCCC.CC(O)C>C(#N)C>[F:25][C:23]1[CH:22]=[C:4]([CH:3]=[C:2]([F:1])[CH:24]=1)[CH2:5][C@@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].[F:25][C:23]1[CH:22]=[C:4]([CH:3]=[C:2]([F:1])[CH:24]=1)[CH2:5][C@H:6]1[CH2:11][C@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 21225753Isopropanol heptaneHCID 68502775HCID 68502775, compound

Product 2

HCID 68500328HCID 68500328, compoundYield 38%HCID 68502775HCID 68502775, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Trans-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.648 g, 1.84 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 70/30, flow rate 18 mL/min) to yield (2S,4S)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate 249 mg (38%), Chiral purity 99.9% ee, Optical rotation [α]D20=+27.1 (acetonitrile, c=1) and (2R,4R)-methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (244 mg, 37%), Chiral purity 99.9% ee, Optical rotation [α]D20=−26.4 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-82a48a1d2ef149bdafa0a413f439332b
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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