Acetic Acid → 1-Benzyl-4-(hydroxymethyl)pyrrolidin-2-one
Reaction equation
[BH4-].[Li+].[CH2:3]([N:10]1[C:14](=[O:15])[CH2:13][CH:12]([C:16](OC)=[O:17])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=O)C>C1COCC1>[CH2:3]([N:10]1[CH2:11][CH:12]([CH2:16][OH:17])[CH2:13][C:14]1=[O:15])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
200 ml of a 2M solution of lithium borohydride in THF were added dropwise to a stirred solution of 100 g of methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate in 600 ml of THF under a nitrogen atmosphere. After 3 hours, the mixture was cooled to 10° C. and treated with 200 ml of 50% aqueous acetic acid. The solvents were removed under reduced pressure and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic extracts were dried and evaporated to dryness to give 92 g of 1-benzyl-4-(hydroxymethyl)-2-pyrrolidinone. This was dissolved in 200 ml of pyridine and the solution was treated with 95 g p-toluenesulphonyl chloride. The solution obtained was stirred for 18 hours and then concentrated. The residue was partitioned between dichloromethane and 2M hydrochloric acid. The organic phase was washed with water, dried and evaporated to dryness. Crystallization of the residue from diethyl ether/n-hexane gave 115 g of 1-benzyl-4-(p-toluenesulphonyloxy)-2-pyrrolidinone of melting point 83°-84° C.
Workup
- customThe solvents were removed under reduced pressure
- customthe residue was partitioned between dichloromethane and saturated sodium bicarbonate solution
- customThe organic extracts were dried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-790d4d298e404292a7775264e8f0d5b9
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292747
Reaction notes
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