Hydrochloric Acid → 3-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

HRID 617344Notes

Reaction equation

HRID 617344 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([CH2:7][O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:3]1.[ClH:15]>C(O)C.CCOCC.[Pd]>[ClH:15].[ClH:15].[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([CH2:7][O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:3]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 542026473-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine

Product 1

HCID 675868713-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A 350 mg sample of the compound from step 72e above was dissolved in 6 mL of ethanol, 35 mg of 10% Pd/C was added, and the reaction mixture was shaken under 4 atm of H2 for 15 hours. The catalyst was removed by filtration, the solvent removed, and the residue was purified by chromatography on silica gel, eluting with 20:1 chloroform:methanol, to give the free base. This compound was treated with HCl in ether according to Example 14c to afford the title compound. MS (DCI/NH3) m/e: 195 (M+H)+, 212 (M+NH4)+. 1H NMR (D2O, 300 MHz) δ: 8.46 (d, 1H, J=2.5 Hz), 8.37 (d, 1H, J=5.1 Hz), 7.93 (m, 1H), 7.90 (dd, 1H, J=5.5, 8.4 Hz), 4.60 (m, 1H), 4.41 (m, 2H), 3.52 (dd, 1H, J=3.7, 2.9 Hz), 3.43 (m, 1H), 2.15-2.35 (m, 2H). Anal. Calc. for C10H14N2O2.2.7 HCl: C, 41.04; H, 5.75; N, 9.57; Found C, 40.90; H, 5.43; N, 9.48.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent removed
  3. customthe residue was purified by chromatography on silica gel
  4. washeluting with 20:1 chloroform
  5. custommethanol, to give the free base

Sources & evidence

ORD record
ord-6001f8c7c7af4ef48b18fe52144fe317
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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