Ethanol heptane → HCID 66732566, compound

HRID 1963655Notes

Reaction equation

HRID 1963655 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=1)[CH2:8][C@H:9]1[CH2:14][C@@H:13]([C:15]2[O:19][NH:18][C:17](=[O:20])[CH:16]=2)[CH2:12][CH2:11][N:10]1[C:21]([O:23][CH3:24])=[O:22])([CH3:4])([CH3:3])[CH3:2].CCCCCCC.CCO>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=1)[CH2:8][C@H:9]1[CH2:14][C@@H:13]([C:15]2[O:19][NH:18][C:17](=[O:20])[CH:16]=2)[CH2:12][CH2:11][N:10]1[C:21]([O:23][CH3:24])=[O:22])([CH3:3])([CH3:4])[CH3:2].[C:1]([C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=1)[CH2:8][C@@H:9]1[CH2:14][C@H:13]([C:15]2[O:19][NH:18][C:17](=[O:20])[CH:16]=2)[CH2:12][CH2:11][N:10]1[C:21]([O:23][CH3:24])=[O:22])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 22502148Ethanol heptaneHCID 68501980HCID 68501980, compound

Product 2

HCID 66732566HCID 66732566, compoundYield 45%HCID 68501980HCID 68501980, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Cis-methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1.358 g, 3.16 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×20), 5 μm particle size, mobile phase: Heptane/EtOH/FA 90/10/0.1, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (550 mg, 40%), Chiral purity 99.6% ee, Optical rotation [α]D20=+14.7 (acetonitrile, c=1) and (2S,4R)-methyl 2-(3,5-di-tert-butylbenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (619 mg, 45%), Chiral purity 99.7% ee, Optical rotation [α]D20=−11.2 (acetonitrile, c=1)

Sources & evidence

ORD record
ord-fad3860c27b34ba4954dc835dc155015
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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