Carbon Dioxide → HCID 24995899, compound

HRID 423675Notes

Reaction equation

HRID 423675 reaction equation
FC(F)(F)C(O)=O.[CH3:8][S:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10].C(=O)=O>CO>[CH3:8][S@@:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 66672997HCID 66672997, compound

Product 1

HCID 24995899HCID 24995899, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic sulfoxide 1-methylethyl 4-[({6-[4-(methylsulfinyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (Example 173, 370 mg) was subjected to Chiral HPLC [column: Chiralpak AS-H, column mobile phase: 65% CO2: 35% MeOH (1 mL/min), pressure 140 bar, temperature 40° C., 215 nm] analysis and then separation to give two (R and S) enantiomers. The title compound (99 mg) was isolated as an off-white solid with Tr of 7.24 min (second eluting peak). The (S) absolute stereochemistry was assigned by Ab initio VCD analysis.

Workup

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

Sources & evidence

ORD record
ord-37298a572d4449a38c5fcc18727ba90a
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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