Carbon Dioxide → 1-methylethyl 4-[(1S)-1-({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate

HRID 423651Notes

Reaction equation

HRID 423651 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][C:14]([O:17][CH:18]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)[CH3:19])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)=O>CO>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][C:14]([O:17][C@H:18]([CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)[CH3:19])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 59177778HCID 59177778, compound

Product 1

HCID 249955901-methylethyl 4-[(1S)-1-({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic 1-methylethyl 4-[1-({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate (prepared as in Example 162) was subjected to Chiral HPLC [column: AS-H, column mobile phase: 85% CO2: 15% MeOH (2 mL/min), pressure 140 bar, temperature 40° C., 215 nm] analysis and then separated to give two (R and S) enantiomers, which were further purified by chromatography on an ISCO silica gel column using 0 to 50% EtOAc/hexanes. The title compound was isolated as a white foam with Tr of 13.37 min (first eluting peak). The (S) absolute stereochemistry was assigned by Ab initio VCD analysis.

Workup

  1. customseparated
  2. customto give two (R and S) enantiomers, which
  3. customwere further purified by chromatography on an ISCO silica gel column

Sources & evidence

ORD record
ord-243cd0c7a7c54e5c98b980e1ab982288
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…