5-Bromo-N-((1RS,2SR)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide → 5-bromo-N-((1S,2R)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

HRID 598249Notes

Reaction equation

HRID 598249 reaction equation
[Br:1][C:2]1[C:3]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[N:4][C:5]([C:18]([F:21])([F:20])[F:19])=[C:6]([CH:17]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[OH:16])=[O:8]>C(O)(C)C.CCCCCCC>[Br:1][C:2]1[C:3]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])=[N:4][C:5]([C:18]([F:21])([F:19])[F:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16])=[O:8]

Participants

3

Reactant 1

HCID 866348035-Bromo-N-((1RS,2SR)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

Product 1

HCID 866348065-bromo-N-((1S,2R)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

Reagents, catalysts & solvents 1

HCID 21225753Isopropanol heptaneSolvent

Procedure

5-Bromo-N-((1RS,2SR)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide (103 g) was subjected to chiral chromatography on ChiralPak AD with 5% isopropanol/n-heptane as eluent. The product eluted as first peak to give after evaporation of the solvent the title compound (42.4 g) as a white solid, MS (ISP) 465.0, 467.0 (M+H)+; [α]D20=−19.8°.

Workup

  1. washThe product eluted as first peak
  2. customto give
  3. customafter evaporation of the solvent the title compound (42.4 g) as a white solid, MS (ISP) 465.0, 467.0 (M+H)+

Sources & evidence

ORD record
ord-d309d5f9f1a8433eb79c9aca722435f6
Source dataset
uspto-grants-2011_03
Patent number
US07897621B2

Reaction notes

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