Methanol → Ethyl acetate methanol ammonium hydroxide

HRID 1243997Notes

Reaction equation

HRID 1243997 reaction equation
[CH3:1][O:2][C:3]1C=C2C(=C[C:12]=1C=O)[N:9](C)C(=O)C(C)(C)C2.C(N([CH2:24][CH3:25])CC)C.Cl.Cl.N[C@H]1CCCN[C@H]1C1C=CC=CC=1.C[OH:42]>C1(C)C=CC=CC=1>[CH3:12][CH2:3][O:2][C:24]([CH3:25])=[O:42].[CH3:1][OH:2].[NH4+:9].[OH-:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 21931813HCID 21931813, compoundHCID 69654807(2S,3S)-2-Phenylpiperidin-3-amine dihydrochloride

Product 1

HCID 21901312Ethyl acetate methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 6-Methoxy-1,3,3-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde (150 mg, 0.6 mmol) in 15 mL of toluene and 2 mL of MeOH was added triethylamine (134 mg, 1.32 mmol) and (2S,3S)-3-amino-2-phenylpiperidine dihydrochloride (150 mg, 0.60 mmol). After heating at reflux for 24 hours and concentrating, the residue was dissolved in CH2Cl2 and treated with sodium triacetoxyborohydride (200 mg). The reaction was stirred at room temperature overnight and quenched with satd NaHCO3. The aqueous portion was extracted with CH2Cl2, and the combined organic phases were washed with water and brine, dried over NaHCO3 and concentrated. Silica gel chromatography (90:9:1 EtOAc/MeOH/NH4OH) gave 52 mg (23%) of a colorless oil. Treatment with excess ethereal HCl and concentration gave 67 mg of the dihydrochloride salt as a white solid.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 24 hours
  3. concentrationconcentrating
  4. dissolutionthe residue was dissolved in CH2Cl2
  5. additiontreated with sodium triacetoxyborohydride (200 mg)
  6. customquenched with satd NaHCO3
  7. extractionThe aqueous portion was extracted with CH2Cl2
  8. washthe combined organic phases were washed with water and brine
  9. dry with materialdried over NaHCO3
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bf9c3c10d82849eb94e10c2360ae14c5
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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