Carbon Dioxide → HCID 86653045, compound

HRID 2060820Notes

Reaction equation

HRID 2060820 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[CH:4][CH:3]=1.C(=O)=O>CO>[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:17])=[O:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 86653044HCID 86653044, compound2×

Product 1

HCID 86653045HCID 86653045, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Separation of the enantiomers comprising cis-N-{2-[(6-bromopyridin-3-yl)oxy]cyclohexyl}propane-2-sulfonamide (7.96 g, 21.1 mmol) was carried out by chiral chromatography. Column: Chiralpak® AD-H, 2.1×25 cm, 5 μm; Mobile phase: 70:30 carbon dioxide:methanol; Flow rate: 65 g/min. The first-eluting compound was enantiomer [N-{(1R,2S)-2-[(6-bromopyridin-3-yl)oxy]cyclohexyl}propane-2-sulfonamide] and the second-eluting peak provided desired product N-{(1S,2R)-2-[(6-bromopyridin-3-yl)oxy]cyclohexyl}propane-2-sulfonamide upon removal of solvent in vacuo. Yield: 3.13 g, 8.30 mmol, 39%. The absolute stereochemistry of these enantiomers was assigned by analogy to Example 5.

Workup

  1. customSeparation of the enantiomers

Sources & evidence

ORD record
ord-f4ca3d1dcb9b422d9c4f652bf7eeeac2
Source dataset
uspto-grants-2012_10
Patent number
US08278457B2

Reaction notes

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