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

HRID 857024Notes

Reaction equation

HRID 857024 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-1c91b9a385a647f59644f0ac0b2da3dc
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

Loading…