Dichloromethane → 2-(2-(R)-pyrrolidinyl)furo[3,2-b]pyridine dihydrochloride
Reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C(Cl)[Cl:30]>>[ClH:30].[ClH:30].[NH:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A 614 mg (2.13 mmol) sample of 2-(1-BOC-2-(R)-pyrrolidinyl)furo[3,2-b]pyridine, from step 3b above, was dissolved in 3 mL of CH2Cl2, and the solution was cooled to 0° C. To this solution was added 3 mL of TFA, and the reaction mixture was stirred at 0° C. for 2 hours. The reaction was quenched with saturated aqueous K2CO3 solution, and the mixture was extracted with CH2Cl2. The organic extract was dried over MgSO4, and the solvent was removed. The residue was purified by chromatography on silica gel and treated with HCl in Et2O as described in Example 1e above to obtain the title compound: 1H NMR (D2O, 300 MHz) δ 2.17-2.69 (m, 4H), 3.52-3.59 (m, 2H), 5.14 (t, 1H, J=5.5 Hz), 7.42 (t, 1H, J=1 Hz), 7.80 (dd, 1H, J=5.6, 8.5 Hz), 8.5 (dt, 1H, J=1, 8.5 Hz), 8.70 (dd, 1H, J=1, 5.5 Hz); MS m/z: 189 (M+H)+, 206 (M+NH4)+ ; Anal. Calcd for C11H12N2O.2.0 HCl.0.5 H2O: C, 48.90; H, 5.60; N, 10.90. Found: C, 48.75; H, 5.74; N, 10.11.
Workup
- customThe reaction was quenched with saturated aqueous K2CO3 solution
- extractionthe mixture was extracted with CH2Cl2
- extractionThe organic extract
- dry with materialwas dried over MgSO4
- customthe solvent was removed
- customThe residue was purified by chromatography on silica gel
- additiontreated with HCl in Et2O
Sources & evidence
- ORD record
- ord-a760f60ce3ae4a2b8ce8ec5719c8082d
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06001849
Reaction notes
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