反応 #7411

反応方程式

6-chloro-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide

lithium bis(trimethylsilyl) amide

lithium bis(trimethylsilyl) amide

bromoacetonitrile

→

title compound

収率 43.0%

6-Chloro-N-(cyanomethyl)-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide

収率 43.0%

溶媒

THF

反応条件

後処理

1. 1
   その他to reach room temperature
2. 2
   その他After reaching room temperature
3. 3
   workup.STIRRINGthe reaction mixture was stirred for a further 18 h
4. 4
   その他quenched by the addition of methanol (1 ml)
5. 5
   濃縮The resultant solution was concentrated under reduced pressure
6. 6
   その他the residue partitioned between water and DCM
7. 7
   その他The organic layer was separated
8. 8
   乾燥dried (over magnesium sulphate)
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The residue was purified by mass

実験手順

A solution of 6-chloro-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide (0.015 g) in THF (2 ml) was cooled to −78° C. under nitrogen, and treated with lithium bis(trimethylsilyl) amide (1.0M solution in THF; 0.042 ml), followed by bromoacetonitrile (0.019 g). The resultant solution was allowed to reach room temperature and stirred for a further 16 h. The mixture was then cooled to −78° C. and further lithium bis(trimethylsilyl) amide (0.042 ml) added. After reaching room temperature, the reaction mixture was stirred for a further 18 h and then quenched by the addition of methanol (1 ml). The resultant solution was concentrated under reduced pressure and the residue partitioned between water and DCM. The organic layer was separated, dried (over magnesium sulphate) and concentrated under reduced pressure. The residue was purified by mass directed preparative h.p.l.c to give the title compound (0.007 g) as a colourless gum.

出典