Triethylamine → 1-tert-Butyl 3-ethyl (3R)-piperidine-1,3-dicarboxylate
Reaction equation
[C:1]([N:8]1[CH2:18][CH2:17][CH2:16][C@@H:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([C@@H]([C@H](C([O-])=O)O)O)([O-])=O.CCN(CC)CC.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(OCC)(=O)C>O1CCOCC1.O>[C:1]([N:8]1[CH2:18][CH2:17][CH2:16][C@@H:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethyl N-Boc-(R)-nipecotate-L-tartrate (24) (10.00 g, 32.5 mol) in 50 mL of dioxane and 50 mL of H2O was cooled in ice-water bath and NEt3 (9 mL) was added with stirring. Stirring and cooling were continued while di-tert-butyl dicarbonate (7.44 g, 1.05 eq.) was introduced. The mixture was warmed to room temperature and stirred for 4 h. 100 mL of Ethyl acetate and 20 mL of H2O were added to mixture. The aqueous layer was extracted with ethyl acetate (2×100 mL). The extracts were combined and washed with aqueous potassium carbonate (sat., 2×50 mL), aqueous HCl (5%, 2×50 mL), brine (50 mL), and dried over anhydrous sodium sulfate, filtered and evaporated to give ethyl N-Boc-(R)-nipecotate as a colorless oil 8.37 g (100%).
Workup
- stirringStirring
- temperaturecooling
- additionwas introduced
- stirringstirred for 4 h
- extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
- washwashed with aqueous potassium carbonate (sat., 2×50 mL), aqueous HCl (5%, 2×50 mL), brine (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-3219931233a1448da6d065e5b61ca9e3
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129228B2
Reaction notes
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