Carbon Dioxide → HCID 59177802, compound

HRID 423626Notes

Reaction equation

HRID 423626 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([O:16][C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)[CH3:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(=O)=O>CO>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]([O:16][C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)[CH3:15])[CH2:10][CH2:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 59177748HCID 59177748, compound

Product 1

HCID 59177802HCID 59177802, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic 5-fluoro-2-{4-[1-({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)ethyl]-1-piperidinyl}pyrimidine (prepared as in Example 153) was subjected to Chiral HPLC [column: OJ-H, column mobile phase: 70% CO2: 30% MeOH (2 mL/min), pressure 140 bar, temperature 40° C., 254 nm] analysis and then separated to give two (R and S) enantiomers. The title compound was isolated as an off-white solid with Tr of 30.59 min (second eluting peak). The (R) 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-09544f365623479cac742bea0f880006
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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