Carbon Dioxide → HCID 59177739, compound

HRID 423674Notes

Reaction equation

HRID 423674 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 59177739HCID 59177739, compoundYield 34.4%

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 (100 mg) was isolated as a white solid with Tr of 3.73 min (first eluting peak). The (R) 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-9ca6f47d0afc4a1dbadd3f73a461a256
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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