Acetic Acid → (1S,2R)-3-(benzyloxy)-1-(2-chlorophenyl)-1-hydroxypropan-2-yl acetate
Reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+].[Ce].[C:26]([OH:29])(=[O:28])[CH3:27]>>[C:26]([O:29][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[OH:11])(=[O:28])[CH3:27]Participants
4
Procedure
To a solution of (±)-2-(benzyloxymethyl)-3-(2-chlorophenyl)oxirane (Preparation example 373, 2.9 g, 10.55 mmole) in Acetic acid (55 mL) was added Cerium Ammonium Nitrate (1.15 g, 2.11 mmole) at room temperature. The mixture was stirred for 18 hr at room temperature. The TLC showed complete consumption of SM. The reaction mixture was quenched with sat'NaHCO3 to pH7 at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (1.2 g, 34%).
Workup
- customconsumption of SM
- customThe reaction mixture was quenched with sat'NaHCO3 to pH7 at 0° C.
- extractionthen extracted with EtOAc
- extractionThe aqueous layer was extracted with EtOAc
- customseparated
- washThe combined organic layer was washed with H2O
- dry with materialdried over MgSO4
- customevaporated under reduced pressure
- customThe crude compound was purified by silica ge column
Sources & evidence
- ORD record
- ord-659fa5bdb0e34050a93ddaef772eba19
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221783B2
Reaction notes
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