Hexane → HCID 68427449, compound

HRID 1931294Notes

Reaction equation

HRID 1931294 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([C@H:14]2[C@H:19]3[CH2:20][CH2:21][C@H:16]([CH2:17][N:18]3[S:22]([C:25]3[N:26]=[CH:27][N:28]([CH3:30])[CH:29]=3)(=[O:24])=[O:23])[CH2:15]2)=[O:13])=[N:9][CH:10]=1)([CH3:3])[CH3:2].CCCCCC>C(O)C>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([CH:14]2[CH:19]3[CH2:20][CH2:21][CH:16]([CH2:17][N:18]3[S:22]([C:25]3[N:26]=[CH:27][N:28]([CH3:30])[CH:29]=3)(=[O:24])=[O:23])[CH2:15]2)=[O:13])=[N:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8058HexaneHCID 68427452HCID 68427452, compound

Product 1

HCID 68427449HCID 68427449, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (561 mg, 1.29 mmol)synthesized in Example 48 was optically resolved using normal-phase chiral HPLC(CHIRALPAK OD 2 cm ø×25 cmL (Daicel Chemical Industries, Ltd.); mobile phase: hexane:ethanol=70:30; flow rate: 10 ml/min; isogradient), and (1R**,4S**,6R**)-N-(5-isopropoxypyridin-2-yl)-2-[(1-methyl-1H-imidazol-4-yl)sulfonyl]-2-azabicyclo[2.2.2]octane-6-carboxamide (retention time: 22 min; 109 mg), and (1S**,4R**,6S**)-N-(5-isopropoxypyridin-2-yl)-2-[(1-methyl-1H-imidazol-4-yl)sulfonyl]-2-azabicyclo[2.2.2]octane-6-carboxamide (retention time: 48.5 min; 115 mg) were obtained.

Sources & evidence

ORD record
ord-133205a24afe4c26b62d746e92b33e67
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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