Sodium Hydroxide → (1-Benzylpyrrolidin-3-yl)methanol

HRID 1789890Notes

Reaction equation

HRID 1789890 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH2:13]([N:20]1[C:24](=O)[CH2:23][CH:22]([C:26](O)=[O:27])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.C1COCC1>[CH2:13]([N:20]1[CH2:24][CH2:23][CH:22]([CH2:26][OH:27])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acidHCID 16684438Red-Al

Product 1

HCID 5176654(1-Benzylpyrrolidin-3-yl)methanolYield 102.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Red-Al (160 mL of a 3.5 M solution in toluene, 560 mmol) was added to a solution of 1-benzyl-5-oxo-pyrrolidine-3-carboxylic acid (20 g, 91 mmol) in dry THF (650 mL) under argon. The reaction mixture was refluxed for 2.5 h and then poured onto a mixture of crushed ice and NaOH (20%). The phases were separated, the aqueous phase was extracted with toluene and the combined organic phases were dried and concentrated under reduced pressure to give 17.9 g of the crude product as a yellow oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 h
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with toluene
  4. customthe combined organic phases were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f65f6c8a26fe4ff3bdf579c9118aad1b
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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