Isopropanol heptane → HCID 68505870, compound

HRID 1963376Notes

Reaction equation

HRID 1963376 reaction equation
[O:1]=[C:2]1[CH:6]=[C:5]([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[C@@H:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH2:8]2)[O:4][NH:3]1.CCCCCCC.CC(O)C>C(#N)C>[O:1]=[C:2]1[CH:6]=[C:5]([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[C@@H:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=3)[CH2:8]2)[O:4][NH:3]1.[O:1]=[C:2]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[C@H:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=3)[CH2:8]2)[O:4][NH:3]1

Participants

5

Reactant 2

HCID 21225753Isopropanol heptaneHCID 68505870HCID 68505870, compound

Product 2

HCID 66734640HCID 66734640, compoundYield 49%HCID 68505870HCID 68505870, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cis-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)phenyl)piperidine-1-carboxylate (311 mg, 0.84 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak IC (250×20), 5 μm particle size, mobile phase: Heptane/IPA 40/60, flow rate 12 mL/min) to yield (2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)-phenyl)piperidine-1-carboxylate (155 mg, 50%), Chiral purity 99.9% ee, Optical rotation [α]D20=−54.4 (acetonitrile, c=1), 1H NMR (400 MHz, cdcl3) δ 1.78-1.90 (m, 1H), 2.08-2.42 (m, 3H), 3.01-3.13 (m, 1H), 3.34-3.48 (m, 1H), 3.65 (s, 3H), 4.09-4.22 (m, 1H), 5.08-5.19 (m, 1H), 5.53 (s, 1H), 7.31-7.50 (m, 4H) and (2S,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)phenyl)piperidine-1-carboxylate (152 mg, 49%), Chiral purity 99.9% ee. Optical rotation [α]D20=−55.7 (acetonitrile, c=1), 1H NMR (400 MHz, cdcl3) δ 1.80-1.90 (m, 1H), 2.11-2.32 (m, 2H), 2.33-2.42 (m, 1H), 3.02-3.12 (m, 1H), 3.36-3.47 (m, 1H), 3.66 (s, 3H), 4.12-4.21 (m, 1H), 5.11-5.17 (m, 1H), 5.53 (s, 1H), 7.33-7.48 (m, 4H).

Sources & evidence

ORD record
ord-feaa5c24ed064d9284eee81cc7e2f6d7
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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