3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester → 2-Methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])([CH3:23])[CH3:22])[CH:15]=2)[CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:27]([O:26][C:24](=[O:25])[C:21]([CH3:22])([O:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH:15]=1)[CH3:23])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester was dissolved in 125 mL of 20% trifluoroacetic acid/methylene chloride and stirred for 20 minutes. The reaction mixture was evaporated under reduced pressure. The resultant oil was taken up in 400 mL water, made basic with 5N aqueous sodium hydroxide and extracted with ethyl acetate (3×300 mL). The extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 11.72 g (54% 3 steps) of 2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester as a pale yellow oil.
Workup
- customThe reaction mixture was evaporated under reduced pressure
- extractionextracted with ethyl acetate (3×300 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-194ae17bff71453381f2ccae56f9eef5
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199243B2
Reaction notes
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