Tetrabutylammonium Fluoride → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]amino-1 (R)-phenylethanol
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]([CH2:23][C:24]1[CH:50]=[CH:49][C:27]([O:28][CH2:29][C@H:30]([NH:32][CH2:33][C@H:34]([O:41][Si](C(C)(C)C)(C)C)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:31])=[CH:26][CH:25]=1)=[O:22]>O1CCCC1.O>[CH3:19][O:20][C:21]([CH2:23][C:24]1[CH:50]=[CH:49][C:27]([O:28][CH2:29][C@H:30]([NH:32][CH2:33][C@@H:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[OH:41])[CH3:31])=[CH:26][CH:25]=1)=[O:22]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
870 mg of tetrabutylammonium fluoride were added to a solution of 510 mg of N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine (prepared as described in Preparation 29) in 15 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was diluted with water, and the aqueous mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 0.23 g of the title compound as crystals, melting at 69°-70° C.
Workup
- extractionthe aqueous mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- customthe solvent was removed by distillation under reduced pressure
- customThe resulting residue was purified by column chromatography through silica gel
Sources & evidence
- ORD record
- ord-7d455146396f497b99a42408951d6218
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576340
Reaction notes
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