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

HRID 1271237Notes

Reaction equation

HRID 1271237 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])C.[H-].C([Al+]CC(C)C)C(C)C>Cl>[CH2:15]([O:14][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[CH:6]=[CH:5][CH2:4][OH:3])=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 53843982HCID 53843982, compound

Product 1

HCID 4266884Benzyl 2-(3-hydroxyprop-1-en-1-yl)pyrrolidine-1-carboxylateYield 46.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 1.86 g of (±)-3-(N-benzyloxycarbonylpyrrolidin-2-yl)acrylic acid ethyl ester in 15 ml of dry dichloromethane1, 12.9 ml of diisobutylaluminum hydride (1M toluene solution) was added dropwise under an argon atmosphere at −70° C. or lower, followed by stirring for one hour. To the reaction solution, 60 ml of 1N hydrochloric acid was added dropwise, and then the mixture was heated to room temperature and extracted with diethyl ether. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.75 g of the desired compound as a colorless oily substance.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-88c1bea237e945628e1dcb36fb0cdf39
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

Loading…