Hydrochloric Acid → 3-(4-Nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene

HRID 1520040Notes

Reaction equation

HRID 1520040 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:17][CH:16]3[N:18](C(OC(C)(C)C)=O)[CH:13]([CH2:14][CH2:15]3)[CH:12]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]>O1CCOCC1.C(Cl)Cl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH2:12][CH:13]3[NH:18][CH:16]([CH2:15][CH2:14]3)[CH:17]=2)=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67981656Tert-butyl 3-(4-nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

Product 1

HCID 97945973-(4-Nitrophenyl)-8-azabicyclo[3.2.1]oct-2-eneYield 76.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (22 mL of a solution 4N in dioxane) was added to a solution of tert-butyl 3-(4-nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (1.97 g; 5.96 mmol; 1.0 eq.) in DCM (20 mL) and the reaction mixture was stirred at RT. After 1 h, the reaction mixture was diluted with DCM and organic phase was washed with NaOH 1N and brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow solid (1.05 g, 76%). 1H NMR (300 MHz, DMSO-d6) δ 8.16 (d, J=9.0 Hz, 2H), 7.65 (d, J=9.0 Hz, 2H), 6.82 (dt, J=6.0 Hz, 1.5 Hz, 1H), 3.74-3.69 (m, 2H), 2.76 (dd, J=17.5 Hz, 4.5 Hz, 1H), 2.17 (dd, J=17.5 Hz, 1.5 Hz, 1H), 1.92-1.68 (m, 3H), 1.56-1.46 (m, 1H). HPLC (max plot) 91.7%; Rt %1.84 min. UPLC/MS: (MS+) 231.2.

Workup

  1. washwas washed with NaOH 1N and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-183fdda14bfe4e27b65e2bc068bcb6d2
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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