m-Chloroperbenzoic acid → {3-[3-(2-Methoxyethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}(1-oxidothiomorpholin-4-yl)methanone

HRID 2091790Notes

Reaction equation

HRID 2091790 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:27]([N:29]3[CH2:34][CH2:33][S:32][CH2:31][CH2:30]3)=[O:28])[CH2:11]2)[O:7][N:6]=1.ClC1C=CC=C(C(OO)=[O:43])C=1>>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:25])([F:24])[F:26])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:27]([N:29]3[CH2:34][CH2:33][S:32](=[O:43])[CH2:31][CH2:30]3)=[O:28])[CH2:11]2)[O:7][N:6]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59606583{3-[3-(2-Methoxyethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}-(thiomorpholin-4-yl)methanone

Product 1

HCID 59606567{3-[3-(2-Methoxyethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}(1-oxidothiomorpholin-4-yl)methanoneYield 39.8%

Procedure

113 mg (0.227 mmol) of the compound from Example 47A were reacted according to General Method 1 with 70.4 mg (0.204 mmol) of meta-chloroperbenzoic acid. Enantiomer separation of 108 mg of the racemate according to Method 9D gave 37.1 mg of the title compound from Example 46 (Enantiomer 1) and 41.8 mg of the title compound from Example 47 (Enantiomer 2).

Workup

  1. customEnantiomer separation of 108 mg of the racemate

Sources & evidence

ORD record
ord-6184c2ae940548d1b6734ed803c958e5
Source dataset
uspto-grants-2013_05
Patent number
US08440657B2

Reaction notes

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