Isopropanol heptane → HCID 66732540, compound

HRID 1963483Notes

Reaction equation

HRID 1963483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][CH:16]([C:18]3[O:22][NH:21][C:20](=[O:23])[CH:19]=3)[CH2:15][CH2:14][N:13]2[C:24]([O:26][CH3:27])=[O:25])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CCCCCCC.CC(O)C>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C@H:12]2[CH2:17][C@@H:16]([C:18]3[O:22][NH:21][C:20](=[O:23])[CH:19]=3)[CH2:15][CH2:14][N:13]2[C:24]([O:26][CH3:27])=[O:25])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10].[F:1][C:2]1[CH:3]=[C:4]([C@@H:12]2[CH2:17][C@H:16]([C:18]3[O:22][NH:21][C:20](=[O:23])[CH:19]=3)[CH2:15][CH2:14][N:13]2[C:24]([O:26][CH3:27])=[O:25])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

5

Reactant 2

HCID 21225753Isopropanol heptaneHCID 66732417HCID 66732417, compound

Product 2

HCID 66732416HCID 66732416, compoundYield 47%HCID 66732540HCID 66732540, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (670 mg, 1.73 mmol) was subjected to chiral preparative HPLC (Column: CelluCoat (250×50), 10 μm particle size, mobile phase: Heptane/EtOH 50/50, flow rate 120 mL/min) to yield (2R,4S)-methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (319 mg, 47%), Chiral purity 99.9% ee, optical rotation [α]D20=+53.4 (acetonitrile, c=0.5) and (2S,4R)-methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (332 mg, 49%), Chiral purity 99.3% ee, Optical rotation [α]D20=−47.6 (acetonitrile, c=0.5).

Sources & evidence

ORD record
ord-4a8acad477ec4cdb86cb28a37c3d29c5
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…