(+/-)-(1S,2R,65)-2-((tert-butoxycarbonyl)amino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-en-1-yl methanesulfonate → (+/-)-(1S,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl methanesulfonate

HRID 705280Notes

Reaction equation

HRID 705280 reaction equation
[CH3:1][S:2]([O:5][C@H:6]1[C@@H:11]([CH3:12])[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-])=O)=[CH:8][C@H:7]1[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:4])=[O:3]>C(O)C.[Pd]>[CH3:1][S:2]([O:5][C@H:6]1[C@@H:11]([CH3:12])[CH2:10][C@@H:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[NH2:19])[CH2:8][C@H:7]1[NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 86705241(+/-)-(1S,2R,65)-2-((tert-butoxycarbonyl)amino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-en-1-yl methanesulfonate

Product 1

HCID 86705243(+/-)-(1S,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl methanesulfonateYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Degass a solution of (+/−)-(1S,2R,6S)-2-((tert-butoxycarbonyl)amino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-en-1-yl methanesulfonate (1.0 equiv.) in Ethanol (0.20 M). To this solution was added Pd/C (0.2 equiv.) and purge with Ar and H2. The mixture was stirred under H2 for 16 hrs. Filter the mixture over cetlite and wash the cake with MeOH. Concentrate the filtrate to yield (+/−)-(1S,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl methanesulfonate in 49% yield). LC/MS (m/z)=400.3 (MH+), Rt=0.62 min.

Workup

  1. custompurge with Ar and H2
  2. filtrationFilter the mixture over cetlite
  3. washwash the cake with MeOH
  4. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-ca7e70a0d0db44d08d61caeadaa26532
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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