8-Cyclohexyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene → 4-(8-Cyclohexyl-8-azabicyclo[3.2.1]oct-3-yl)aniline

HRID 1520042Notes

Reaction equation

HRID 1520042 reaction equation
[CH:1]1([N:7]2[CH:12]3[CH2:13][CH2:14][CH:8]2[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.[Pd]>[CH:1]1([N:7]2[CH:8]3[CH2:14][CH2:13][CH:12]2[CH2:11][CH:10]([C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:9]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 679816248-Cyclohexyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene

Product 1

HCID 679814114-(8-Cyclohexyl-8-azabicyclo[3.2.1]oct-3-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-cyclohexyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene (230 mg; 0.74 mmol; 1.0 eq.) in EtOH (7 mL) was passed twice at 1 mL/min through the H-Cube using a cartridge of Pd/C under full H2 at 250. The solution was then concentrated under reduced pressure to give the title compound as a 66:33 mixture of the endo:exo isomers (163 mg; 78%). 1H NMR (DMSO) δ 6.94 (d, J=8.3 Hz, 1.3H), 6.87 (d, J=8.3 Hz, 0.7H), 6.48-6.45 (m, 2H), 4.78 (bs, 2H), 3.47 (m, 2H), 2.84-2.70 (m, 1H), 2.19-2.07 (m, 2H), 1.90-1.82 (m, 3H), 1.72-1.63 (m, 5H), 1.54-1.46 (m, 2H), 1.40-1.33 (m, 2H), 1.27-0.98 (m, 5H). HPLC (max plot) 65.3%; Rt %2.25 min. UPLC/MS: (MS+) 285.4.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-68701a893759400592ead3fd009b91a8
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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