Isopropanol heptane → (2S,4R)-Methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate

HRID 1963508Notes

Reaction equation

HRID 1963508 reaction equation
[CH:1]1([O:7][CH2:8][C@H:9]2[CH2:14][C@@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH3:24])=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCCCCCC.CC(O)C>C(#N)C>[CH:1]1([O:7][CH2:8][C@H:9]2[CH2:14][C@@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH3:24])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:1]1([O:7][CH2:8][C@@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2[C:21]([O:23][CH3:24])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 21225753Isopropanol heptaneHCID 68502091(2R,4S)-Methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate

Product 2

HCID 66732848(2S,4R)-Methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylateYield 46%HCID 68502091(2R,4S)-Methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-Methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (423 mg, 1.25 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak IC (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 70/30, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (190 mg, 45%), Chiral purity 98.3% ee, Optical rotation [α]D20=+55.9 (acetonitrile, c=1) and (2S,4R)-methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (194 mg, 46%), Chiral purity 98.6% ee, Optical rotation [α]D20=−55.4 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-f01565ae5bf4431a8517dd13c688458d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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