Sodium Bicarbonate → Benzyl 2-(3-hydroxyprop-1-en-1-yl)pyrrolidine-1-carboxylate

HRID 744142Notes

Reaction equation

HRID 744142 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=[CH:17][C:18](OCC)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=[CH:17][CH2:18][OH:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 21225700DiisobutylaluminumhydrideHCID 53843982HCID 53843982, compoundHCID 54132542Phenylmethyl 2-(3-ethoxy-3-oxo-1-propen-1-yl)-1-piperidinecarboxylate

Product 2

HCID 4266884Benzyl 2-(3-hydroxyprop-1-en-1-yl)pyrrolidine-1-carboxylateHCID 544205411-(N-benzyloxycarbonyl-piperid-2-yl)-3-hydroxypropene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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-hydroxypropene or 1-(N-benzyloxycarbonyl-piperid-2-yl)-3-hydroxypropene.

Workup

  1. temperatureto warmed to room temperature over the course of 2 hours
  2. extractionthe aqueous mixture was extracted with ethyl acetate (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-52d245265faf412fa3ce6f9787fecee9
Source dataset
uspto-grants-1996_09
Patent number
US05559129

Reaction notes

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