Isopropanol heptane → HCID 66739246, compound

HRID 1963406Notes

Reaction equation

HRID 1963406 reaction equation
[C:1]([C:5]1[S:9][C:8]([C@H:10]2[CH2:15][C@@H:14]([C:16]3[O:20][NH:19][C:18](=[O:21])[CH:17]=3)[CH2:13][CH2:12][N:11]2[C:22]([O:24][CH3:25])=[O:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCCCCCC.CC(O)C>C(#N)C>[C:1]([C:5]1[S:9][C:8]([C@H:10]2[CH2:15][C@@H:14]([C:16]3[O:20][NH:19][C:18](=[O:21])[CH:17]=3)[CH2:13][CH2:12][N:11]2[C:22]([O:24][CH3:25])=[O:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3].[C:1]([C:5]1[S:9][C:8]([C@@H:10]2[CH2:15][C@H:14]([C:16]3[O:20][NH:19][C:18](=[O:21])[CH:17]=3)[CH2:13][CH2:12][N:11]2[C:22]([O:24][CH3:25])=[O:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21225753Isopropanol heptaneHCID 66739246HCID 66739246, compound

Product 2

HCID 66739246HCID 66739246, compoundYield 49%HCID 66742114HCID 66742114, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-methyl 2-(5-tert-butylthiophen-2-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (436 mg, 1.2 mmol) was subjected to chiral preparative HPLC (Column: CelluCoat (250×20 mm), 5 μm particle size, mobile phase: Heptane/EtOH 80/20, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(5-tert-butylthiophen-2-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (212 mg, 49%), Chiral purity 98.7% ee, Optical rotation [α]D20=+3.0 (acetonitrile, c=1.0), 1H NMR (600 MHz, cdcl3) δ 1.34 (s, 9H), 1.55-1.68 (m, 1H), 1.90-2.04 (m, 2H), 2.49 (d, 1H), 3.12 (s, br., 2H), 3.76 (s, 3H), 4.19 (d, br., 1H), 5.60-5.87 (m, 2H), 6.59-6.69 (m, 2H) and (2S,4R)-methyl 2-(5-tert-butylthiophen-2-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (210 mg, 48%), Chiral purity 99.3% ee, Optical rotation [α]D20=−1.1 (acetonitrile, c=1.0), 1H NMR (600 MHz, cdcl3) δ 1.33 (s, 9H), 1.54-1.66 (m, 1H), 1.88-2.03 (m, 2H), 2.48 (d, 1H), 3.11 (s, br., 2H), 3.74 (s, 3H), 4.17 (d, br., 1H), 5.58-5.85 (m, 2H), 6.58-6.67 (m, 2H).

Sources & evidence

ORD record
ord-7a2a998822c743e0b289a633390f33a8
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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