Carbon Dioxide → HCID 59177825, compound

HRID 423602Notes

Reaction equation

HRID 423602 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: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])=[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: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])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 59177770HCID 59177770, compound

Product 1

HCID 59177825HCID 59177825, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic 1-methylethyl 4-[1-({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)ethyl]-1-piperidinecarboxylate (prepared as in Example 140) was subjected to Chiral HPLC [column: AS-H, column mobile phase: 80% CO2: 20% MeOH (2 mL/min), pressure 140 bar, temperature 40° C., 280 nm] analysis and then separated to give two (R and S) enantiomers. The title compound was isolated as a white foam with Tr of 13.23 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-15ce7edb52444f52946c6af9883c3845
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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