Reaktion #729114

Reaktionsgleichung

ethyl acetate petroleum ether

2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine

lithium 3-(3-methoxypyrrolidin-1-yl)benzenesulfinate

NCS

→

3-(3-methoxypyrrolidin-1-yl)benzene-1-sulfonyl chloride

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 250 mL round bottom flask was placed
2. 2
   Sonstigeto react
3. 3
   Sonstigethe ice bath was removed
4. 4
   Sonstigeto react for an additional 25 minutes at room temperature
5. 5
   WaschenThe resulting mixture was washed 2 times with 50 mL of NaHSO3 and 2 times with 50 mL of brine
6. 6
   TrocknenThe mixture was dried over Na2SO4
7. 7
   Einengenconcentrated by evaporation under vacuum
8. 8
   Sonstigea rotary evaporator
9. 9
   SonstigeThe residue was purified
10. 10
    Waschenby eluting through a column with a 2:3 ethyl acetate/petroleum ether solvent system
11. 11
    SonstigeThis resulted in 6.6 g (82.5%) of 3-(3-methoxypyrrolidin-1-yl)benzene-1-sulfonyl chloride as yellow oil

Vorschrift

Into a 250 mL round bottom flask was placed a solution of lithium 3-(3-methoxypyrrolidin-1-yl)benzenesulfinate (12 g, 29.15 mmol) in dichloromethane (100 mL). To the above was added NCS (4.48 g, 33.56 mmol) in several batches, while cooling to a temperature of 0° C. over a time period of 10 minutes. The resulting solution was allowed to react, with stirring, for 15 minutes while the temperature was maintained at 0° C. in a bath of H2O/ice, then the ice bath was removed and the solution was allowed to react for an additional 25 minutes at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether 5=1:1). The resulting mixture was washed 2 times with 50 mL of NaHSO3 and 2 times with 50 mL of brine. The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a column with a 2:3 ethyl acetate/petroleum ether solvent system. This resulted in 6.6 g (82.5%) of 3-(3-methoxypyrrolidin-1-yl)benzene-1-sulfonyl chloride as yellow oil.

Quelle