Trifluoroacetic acid → 8-(3-Chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane

HRID 1246710Notes

Reaction equation

HRID 1246710 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:13]3[CH2:14][CH2:15][CH:9]2[CH2:10][N:11](C(OC(C)(C)C)=O)[CH2:12]3)=[N:4][CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([N:8]2[CH:9]3[CH2:15][CH2:14][CH:13]2[CH2:12][NH:11][CH2:10]3)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21904766Tert-butyl 8-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Product 1

HCID 219047698-(3-Chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 8-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (285 mg, 880 μmol) in dry dichloromethane (2 mL) was treated with trifluoroacetic acid (2 mL). After stirring at ambient temperature for 30 minutes, the mixture was concentrated under reduced pressure and the residue was treated with 1N sodium hydroxide solution. The mixture was extracted with ethyl acetate and the organic phase was concentrated under reduced pressure to provide the title compound. MS (DCI/NH3) m/z: 224 (M+H)+; 1H NMR (CDCl3) δ 1.87 (m, 2H), 1.97 (m, 2H), 2.75 (dd, 2H), 3.24 (dd, 2H), 4.44 (dd, 2H), 6.73 (dd, 1H), 7.54 (dd, 1H), 8.08 (dd, 1H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionthe residue was treated with 1N sodium hydroxide solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. concentrationthe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc84f5e3e04a492ab1d5296fe321e52e
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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