Reaktion #159537

Reaktionsgleichung

cyclobutanone

butyllithium

N-benzylmethanesulfonamide

acetic acid

→

product

(1-Hydroxycyclobutyl)methanesulfonamide

Lösungsmittel

hexane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto come to room temperature
2. 2
   workup.STIRRINGwhile stirring
3. 3
   Sonstigethe volatile constituents were removed under reduced pressure
4. 4
   workup.ADDITIONThe residue was taken up in a mixture of 50 ml of ethyl acetate and 50 ml of aqueous sodium hydrogencarbonate solution
5. 5
   Extraktionthe aqueous phase was extracted again with 50 ml of ethyl acetate
6. 6
   TrocknenThe combined organic phases were dried over MgSO4
7. 7
   Einengenconcentrated by rotary evaporation
8. 8
   SonstigeThe crude product thus obtained
9. 9
   Sonstigewas recrystallized from ethyl acetate/n-heptane
10. 10
    workup.DISSOLUTIONdissolved in 20 ml of methanol and, with addition of 0.36 g of 20% Pd(OH)2/C
11. 11
    workup.STIRRINGstirred under a hydrogen atmosphere at 60° C. for 3 hours
12. 12
    FiltrationAfter filtration
13. 13
    Sonstigeto remove the solid residues

Vorschrift

Under inert gas, 2.00 g of N-benzylmethanesulfonamide were initially charged in 20 ml of THF, then, at a temperature of −78° C., 13.50 ml of a 1.6 N solution of butyllithium in hexane were added dropwise and the mixture was stirred at constant temperature for 5 minutes. The reaction solution was admixed with 3.23 ml of cyclobutanone and allowed to come to room temperature while stirring. After the addition of 1.24 ml of acetic acid, the volatile constituents were removed under reduced pressure. The residue was taken up in a mixture of 50 ml of ethyl acetate and 50 ml of aqueous sodium hydrogencarbonate solution, and the aqueous phase was extracted again with 50 ml of ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. The crude product thus obtained was recrystallized from ethyl acetate/n-heptane, then dissolved in 20 ml of methanol and, with addition of 0.36 g of 20% Pd(OH)2/C, stirred under a hydrogen atmosphere at 60° C. for 3 hours. After filtration to remove the solid residues, the filtrate was freed of the solvent under reduced pressure. This gave the product (1.07 g) with a molecular weight of 165.2 g/mol (C5H11NO2S).

Quelle