Trifluoroacetic acid → 1-{4-[1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}cyclopropane carboxylic acid
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([C:24]([OH:26])=[O:25])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.O1CCCC1.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.C(N(CC)C(C)C)(C)C>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([C:24]([OH:26])=[O:25])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-{4-[1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl]phenyl}cyclopropanecarboxylic acid (300 mg, prepared as described in example 210, steps 1 & 2) and trifluoroacetic acid 2 mL was stirred at rt for 5 h. The reaction mixture was then concentrated. The crude product was dissolved in tetrahydrofuran (4 mL, 0.05 mol) and to this was added di-tert-butyldicarbonate (333 mg, 0.00152 mol) and N,N-diisopropylethylamine (6.0×10−2 μL, 0.0035 mol). The mixture was stirred at rt for 5 h and then diluted with AcOEt, washed with saturated NaHCO3 aqueous solution and 1M HCl successively, dried with MgSO4, and concentrated in-vacuo to afford the desired product.
Workup
- concentrationThe reaction mixture was then concentrated
- stirringThe mixture was stirred at rt for 5 h
- washwashed with saturated NaHCO3 aqueous solution and 1M HCl successively
- dry with materialdried with MgSO4
- concentrationconcentrated in-vacuo
Sources & evidence
- ORD record
- ord-ab860553b6e040fd93264483ec7abe62
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058288B2
Reaction notes
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