1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanone → 2-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]propane-2-ol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[NH:15][C@@H:14]([C:16](=[O:18])[CH3:17])[CH2:13][O:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[CH3:19][Mg]Br>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[F:9][C:6]1[CH:5]=[C:4]([C@H:10]2[NH:15][C@@H:14]([C:16]([OH:18])([CH3:19])[CH3:17])[CH2:13][O:12][CH2:11]2)[CH:3]=[C:2]([F:1])[C:7]=1[F:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]ethanone (529 mg) in tetrahydrofuran (25 mL) was, under a nitrogen atmosphere, dropwise added methylmagnesium bromide (0.97 M tetrahydrofuran solution, 4.63 mL) at 0° C. The resultant solution was stirred for 1 hour at the same temperature, and then diluted with aqueous ammonium chloride and ethyl acetate. The organic layer was partitioned, washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate), to thereby obtain the titled compound (330 mg). The physical properties of this crude product were as follows.
Workup
- customat 0° C
- customThe organic layer was partitioned
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customSolvent was removed by distillation under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate)
Sources & evidence
- ORD record
- ord-7a4bb6e137424f54a88c761334c3e19e
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737141B2
Reaction notes
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