Carbon Dioxide → 2-[((1S)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl)oxy]-5-[4-(methylsulfonyl)phenyl]pyrazine

HRID 423632Notes

Reaction equation

HRID 423632 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]([O:17][C:18]3[CH:23]=[N:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=4)=[CH:20][N:19]=3)[CH3:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:3].C(=O)=O>CO>[CH3:3][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][CH:12]([C@@H:15]([O:17][C:18]3[CH:23]=[N:22][C:21]([C:24]4[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=4)=[CH:20][N:19]=3)[CH3:16])[CH2:13][CH2:14]2)[O:6][N:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 59177753Racemic 2-[(1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl)oxy]-5-[4-(methylsulfonyl)phenyl]pyrazine

Product 1

HCID 249955882-[((1S)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl)oxy]-5-[4-(methylsulfonyl)phenyl]pyrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic 2-[(1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl)oxy]-5-[4-(methylsulfonyl)phenyl]pyrazine (prepared as in Example 156) was subjected to Chiral HPLC [column: AS-H, column mobile phase: 70% CO2: 30% MeOH (2 mL/min), pressure 140 bar, temperature 40° C., 215 nm] analysis and then separated to give two (R and S) enantiomers. The title compound was isolated as an off-white solid with Tr of 25.83 min (second eluting peak). The (S) absolute stereochemistry was assigned by Ab initio VCD analysis.

Workup

  1. customseparated
  2. customto give two (R and S) enantiomers

Sources & evidence

ORD record
ord-896a44d18461498788e2c46555060e6f
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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