Dichloromethane → 2-(2-(S)-pyrrolidinyl)furo[3,2-b]pyridine dihydrochloride

HRID 611555Notes

Reaction equation

HRID 611555 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(Cl)[Cl:23]>C(O)(C(F)(F)F)=O.Cl>[ClH:23].[ClH:23].[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]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 153897342-(1-BOC-2-(S)-pyrrolidinyl)furo[3,2-b]pyridine

Product 1

HCID 702073442-(2-(S)-pyrrolidinyl)furo[3,2-b]pyridine dihydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A 980 mg sample of 2-(1-BOC-2-(S)-pyrrolidinyl)furo[3,2-b]pyridine, from Example 1d above, was dissolved in a solution of TFA in CH2Cl2 at 0° C. and stirred under N2 while warming to room temperature. The reaction mixture was diluted with 1 N HCl, and the aqueous layer was separated. The aqueous solution was adjusted to pH 10 with K2CO3, and the mixture was extracted with CH2Cl2. The solution was dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel and treated with HCl in Et2O as described in Example 1e to obtain 280 mg of title compound: 1H NMR (CDCl3, 300 MHz) δ 2.17-2.52 (m, 3H), 2.65 (m, 1H), 3.57 (dt, 2H, J=1.5, 7.5 Hz), 5.15 (t, 1H, J=8 Hz), 7.44 (s, 1H), 7.84 (dd, 1H, J=6, 8.5 Hz), 8.5 (dt, 1H, J=1, 8.5 Hz), 8.70 (dd, 1H, J=1, 6 Hz). MS m/z: 189 (M+H)+, 206 (M+NH4)+ ; Anal. Calcd for C11H12N2O.2.0 HCl: C, 50.59; H, 5.40; N, 10.73. Found: C, 50.52; H, 5.26; N, 10.50.

Workup

  1. customthe aqueous layer was separated
  2. extractionthe mixture was extracted with CH2Cl2
  3. dry with materialThe solution was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel
  6. additiontreated with HCl in Et2O

Sources & evidence

ORD record
ord-0d5fbd627afe4a6892f4d3d929a5d6f1
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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