Hexane → HCID 45482507, compound

HRID 1931293Notes

Reaction equation

HRID 1931293 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][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])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CCCCCC>C(O)(C)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:23])=[O:24])[CH2:15]2)=[O:13])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8058HexaneHCID 68427355HCID 68427355, compound

Product 1

HCID 45482507HCID 45482507, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The compound (60 mg, 0.138 mmol) synthesized in Example 26 was optically resolved using normal-phase chiral HPLC(CHIRALPAK AD 2 cm ø×25 cmL (Daicel Chemical Industries, Ltd.); mobile phase: hexane:isopropyl alcohol=60:40; flow rate: 10 ml/min; isogradient), and (1R**,4S**,6R**)-N-(4-isopropoxyphenyl)-2-[(1-methyl-1H-imidazol-4-yl)sulfonyl]-2-azabicyclo[2.2.2]octane-6-carboxamide (retention time: 14.2 min; 26.6 mg), and (1S**,4R**,6S**)-N-(4-isopropoxyphenyl)-2-[(1-methyl-1H-imidazol-4-yl)sulfonyl]-2-azabicyclo[2.2.2]octane-6-carboxamide (retention time: 30.7 min; 29.4 mg) were obtained.

Sources & evidence

ORD record
ord-bc820bbdfc4b47de9a255a0255dbd6e2
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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