Trifluoroacetic acid → 3-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

HRID 987564Notes

Reaction equation

HRID 987564 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](O)([C:16]1[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=1)[CH2:12]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[C:11]1[CH2:12][CH:13]2[NH:8][CH:9]([CH2:15][CH2:14]2)[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 205955433-Hydroxy-3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 119560113-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-eneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (6.80 g, 19.3 mmol) and 10 mL TFA are stirred at 23° C. in 80 mL of CH2Cl2 for 2.5 h. The volatiles are removed and the residue partitioned between 100 mL of saturated NaHCO3 and 100 mL EtOAc. The aqueous layer is extracted with 2×50 mL EtOAc, and the combined organics are washed with 3×50 mL H2O, 1×50 mL brine, dried over MgSO4, filtered, and stripped to give 4.50 g (19.1 mmol, a 100% yield) of the title compound as a white solid. MS (ES) m/z (relative intensity): 236 (M++H, 100).

Workup

  1. customThe volatiles are removed
  2. customthe residue partitioned between 100 mL of saturated NaHCO3 and 100 mL EtOAc
  3. extractionThe aqueous layer is extracted with 2×50 mL EtOAc
  4. washthe combined organics are washed with 3×50 mL H2O, 1×50 mL brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto give 4.50 g (19.1 mmol

Sources & evidence

ORD record
ord-2904ed5f63dd4f9da36117a08444fd05
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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