Trifluoroacetic acid → 5,6-Dichloro-2-(2-(R)-pyrrolidinyl)furo[3,2-b]pyridine

HRID 611586Notes

Reaction equation

HRID 611586 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C@H:11]3[CH2:15][CH2:14][CH2:13][N:12]3C(OC(C)(C)C)=O)[O:10][C:5]2=[CH:4][C:3]=1[Cl:23].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C@H:11]3[CH2:15][CH2:14][CH2:13][NH:12]3)[O:10][C:5]2=[CH:4][C:3]=1[Cl:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 543798315,6-Dichloro-2-(1-t-butyloxycarbonyl-2-(R)-pyrrolidinyl)furo[3,2-b]pyridin

Product 1

HCID 538109675,6-Dichloro-2-(2-(R)-pyrrolidinyl)furo[3,2-b]pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6-Dichloro-2-(1-t-butyloxycarbonyl-2-(R)-pyrrolidinyl)furo[3,2-b]pyridine (355 mg, 1.0 mmol) was dissolved in CH2Cl2 (3 mL) and TFA (3 mL) was added at ambient temperature. After stirring for 1 hour, the solvent was removed and the residue was redissolved in CH2Cl2 and washed with saturated K2CO3 solution, dried (MgSO4) and concentrated. The crude product was chromatographed (silica gel; CHCl3 /MeOH, 98:2) to afford a solid (220 mg, 87%): 1H NMR (CDCl3, 300 MHz) δ 1.81-2.05 (m, 3H), 2.15-2.29 (m, 1H), 3.04-3.20 (m, 2H), 4.39-4.42 (m, 1H), 6.70 (s, 1H), 7.80 (s, 1H); MS (CI/NH3) m/z: 257 (M+H)+.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was redissolved in CH2Cl2
  3. washwashed with saturated K2CO3 solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was chromatographed (silica gel; CHCl3 /MeOH, 98:2)

Sources & evidence

ORD record
ord-3b9bba6406f641a5b3e450497a948d3a
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

Loading…