Hydrochloric Acid → Benzyl 2-formylpyrrolidine-1-carboxylate

HRID 1271236Notes

Reaction equation

HRID 1271236 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=O.Cl>ClCCl.[H-].C([Al+]CC(C)C)C(C)C>[CH2:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][CH:5]1[CH:3]=[O:2])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3387867HCID 3387867, compound

Product 1

HCID 11064320Benzyl 2-formylpyrrolidine-1-carboxylateYield 44.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21225700DiisobutylaluminumhydrideSolvent

Procedure

To a solution of 12.00 g of (±)-N-benzyloxycarbonyl-2-pyrrolidine carboxylic acid methyl ester in 50 ml of dry dichloromethane, 50 ml of diisobutylaluminum hydride (1M toluene solution) was added dropwise under an argon atmosphere at −70° C. or lower, followed by stirring for 2 hours. To the reaction solution, 230 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 4.72 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-20fe10db639f4d968fbe3471925b1b41
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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