Sodium Bicarbonate → 1-(N-benzyloxycarbonyl-piperid-2-yl)-3-hydroxypropene
Reaction equation
C(OC(N1CCCC1C=CC(OCC)=O)=O)C1C=CC=CC=1.C([O:25][C:26](=O)[CH:27]=[CH:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][N:30]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])C.[H-].C([Al+]CC(C)C)C(C)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:38]([O:37][C:35]([N:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH:29]1[CH:28]=[CH:27][CH2:26][OH:25])=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of either ethyl 3-(N-benzyloxycarbonylpyrrolidin-2-yl)-2-propenoate or ethyl-3-(N-benzyloxycarbonylpiperid-2-yl)-2-propenoate (R, or S, or racemate, 10.00 mmol) in anhydrous tetrahydrofuran (75 mL) at -78° C. under nitrogen was added dropwise a solution of diisobutylaluminium hydride (1.0M in hexanes, 12.0 mL, 22.0 mmol, 2.2 eq). The resulting solution was stirred at -78° C. under nitrogen for 30 minutes. The reaction solution was then allowed to warmed to room temperature over the course of 2 hours. A saturated solution of sodium hydrogen carbonate (50 mL) was added, and the aqueous mixture was extracted with ethyl acetate (3×50 mL). The extracts were combined, dried (MgSO4), and evaporated under reduced pressure. Column chromatography of the residue with diethyl ether/hexanes [1:1] afforded either 1-(N-benzyloxycarbonylpyrrolidin-2-yl)-3-hydropropene or 1-(N-benzyloxycarbonyl-piperid-2-yl)-3-hydroxypropene.
Workup
- temperatureto warmed to room temperature over the course of 2 hours
- extractionthe aqueous mixture was extracted with ethyl acetate (3×50 mL)
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1a3f057776a5400fb0958329e0441fc3
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05559246
Reaction notes
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