Carbon Dioxide → HCID 59177784, compound

HRID 423604Notes

Reaction equation

HRID 423604 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH:18]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)[CH2:19][CH3:20])=[CH:13][CH:12]=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:16]=[CH:15][C:14]([O:17][C@H:18]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][CH:30]([CH3:31])[CH3:32])=[O:28])[CH2:23][CH2:22]3)[CH2:19][CH3:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 59177829HCID 59177829, compound

Product 1

HCID 59177784HCID 59177784, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic 1-methylethyl 4-[1-({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy) propyl]-1-piperidinecarboxylate (prepared as in Example 142) was subjected to Chiral HPLC [column: AS-H, column mobile phase: 80% CO2: 20% 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 a white foam with Tr of 14.60 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-b73ead3520ba4373ab4285cebc418877
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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