3-Methoxybenzylamine → HCID 57754052, compound

HRID 226213

Reaction equation

HRID 226213 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]([C@H:18]1[CH2:20][O:19]1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[O-]S(C(F)(F)F)(=O)=O.[Li+].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH2:37].[Cl-].[NH4+]>C(#N)C>[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=1)[C@H:18]([OH:19])[CH2:20][NH:37][CH2:36][C:35]1[CH:38]=[CH:39][CH:40]=[C:33]([O:32][CH3:31])[CH:34]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 211563-MethoxybenzylamineHCID 25517Ammonium ChlorideHCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 86616462(1R,2S)-[2-(3,4-difluoro-phenyl)-1-oxiranyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 57754052HCID 57754052, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (1R,2S)-[2-(3,4-difluoro-phenyl)-1-oxiranyl-ethyl]-carbamic acid tert-butyl ester (0.03 g, 0.1 mmol) in acetonitrile (1 mL) was treated with lithium triflate (0.032 g, 0.2 mmol) and stirred at ambient temperature for 20 minutes. Then 3-methoxybenzylamine (0.016 mL, 0.12 mmol) was added to the reaction neat in one portion. The reaction was stirred at ambient temperature for 14 hours. The reaction was poured into saturated ammonium chloride solution (5 mL), extracted with ethyl acetate, the organic phase separated, dried (MgSO4) and the solvent removed at reduced pressure. The product was obtained as an oil and used without further purification (0.041 g, 94%). MS: 437 (M+H, 100%).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 14 hours
  2. extractionextracted with ethyl acetate
  3. customthe organic phase separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed at reduced pressure
  6. customThe product was obtained as an oil
  7. customused without further purification (0.041 g, 94%)

Sources & evidence

ORD record
ord-102b0fd138274c048ebe5de232edecef
Source dataset
uspto-grants-2009_07
Patent number
US07557137B2

Linked notes

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