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

HRID 1394078Notes

Reaction equation

HRID 1394078 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:14][CH:13]3[N:15](C(OC(C)(C)C)=O)[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[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[CH2:9][CH:10]3[NH:15][CH:13]([CH2:12][CH2:11]3)[CH2:14]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21904762Tert-butyl 3-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 219047683-(3-Chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (419 mg, 1.29 mmol) in dry dichloromethane (5 mL) was treated with trifluoroacetic acid and stirred at room temperature for an hour. 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 (ESI) m/z: 224 (M+H)+; 1H NMR (CDCl3) δ 1.86 (m, 2H), 2.09 (m, 2H), 3.09 (d, 2H), 3.63 (m, 4H), 6.81 (dd, 1H), 7.56 (dd, 1H), 8.16 (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-c0afab7d92194d478364834f77f076e3
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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