Trifluoroacetic acid → Ammonium Hydroxide

HRID 617333Notes

Reaction equation

HRID 617333 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][CH3:15])[C@@H:9]1[CH2:16][O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)(OC(C)(C)C)=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH-:2].[NH4+:8].[CH2:13]([C@H:10]1[CH2:11][CH2:12][NH:8][C@H:9]1[CH2:16][O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67585080HCID 67585080, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67586569HCID 67586569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 160 mg (0.5 mmol) sample of 3-(cis-1-BOC-3-propyl-2-pyrrolidinylmethoxy)pyridine, from step 60b above, was dissolved in 2 mL of methylene chloride and stirred with 1 mL of TFA for 16 hours at room temperature. The solvent was removed under vacuum, and the residue was adjusted to pH 8 with NaHCO3. The mixture was extracted with methylene chloride, and the extract was dried over MgSO4The residue was purified by chromatography on silica gel, eluting with 10:2:0.2 CHCl3: methanol:ammonium hydroxide, to give 60 mg of the title product. MS (DCI/NH3) m/e: 221 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.33 (m, 1H), 8.24 (m, 1H), 7.22 (m, 2H), 4.10 (m, 1H), 4.00 (m, 1H), 3.69 (m, 1H), 3.24 (m, 1H), 3.07 (m, 1H), 2.33 (m, 1H), 2.07 (m, 1H), 1.65 (m, 1H), 1.39 (m, 4H), 0.92 (m, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. extractionThe mixture was extracted with methylene chloride
  3. customthe extract was dried over MgSO4The residue
  4. customwas purified by chromatography on silica gel
  5. washeluting with 10:2:0.2 CHCl3

Sources & evidence

ORD record
ord-16b10c73de9e4544bc2e86801ddccfaa
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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