HCID 131730375, compound → HCID 66732616, compound

HRID 1963351Notes

Reaction equation

HRID 1963351 reaction equation
[CH3:1][C:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:20])[CH2:3][C@H:4]1[CH2:9][C@H:8]([C:10]2[O:14][NH:13][C:12](=[O:15])[CH:11]=2)[CH2:7][CH2:6][N:5]1[C:16]([O:18][CH3:19])=[O:17]>CCCCCCC.CC(O)C>[CH3:20][C:2]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:1])[CH2:3][C@@H:4]1[CH2:9][C@@H:8]([C:10]2[O:14][NH:13][C:12](=[O:15])[CH:11]=2)[CH2:7][CH2:6][N:5]1[C:16]([O:18][CH3:19])=[O:17]

Participants

3

Reactant 1

HCID 131730375HCID 131730375, compound

Product 1

HCID 66732616HCID 66732616, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 21225753Isopropanol heptaneSolvent

Procedure

Racemic trans-methyl 2-(2-methyl-2-phenylpropyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (0.82 g, 2.28 mmol) was subjected to chiral separation using Chiralcel IC, mobile phase heptane/IPA 80/20 at 40° C. which resulted in (2S,4S)-methyl 2-(2-methyl-2-phenylpropyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.361 g, 1.01 mmol).

Workup

  1. customat 40° C.

Sources & evidence

ORD record
ord-0433cc9c438c4c39a2666ce5b9be7d35
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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