Trifluoroacetic acid → (R)-2-Amino-2-(4-fluoro-3-morpholin-4-yl-phenyl)-ethanol

HRID 1825042Notes

Reaction equation

HRID 1825042 reaction equation
C(O)(C(F)(F)[F:4])=O.C(OC(=O)[NH:14][C@H:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:19]=1F)[CH2:16][OH:17])(C)(C)C>C(Cl)Cl>[NH2:14][C@H:15]([C:18]1[CH:23]=[CH:22][C:21]([F:4])=[C:20]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:19]=1)[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69527704(R)-[1-(fluoro-3-morpholin-4-yl-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 57419699(R)-2-Amino-2-(4-fluoro-3-morpholin-4-yl-phenyl)-ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of TFA (5 mL) and (R)-[1-(fluoro-3-morpholin-4-yl-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (1.2 g) in methylene chloride (15 mL) was stirred for 2 h. After concentration, the residue was neutralized with 10 N NaOH and extracted with methylene chloride. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give the title compound as a solid (720 mg).

Workup

  1. concentrationAfter concentration
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-951e9597107b4e8b92cde7d23d264cc3
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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