반응 #7411

반응 방정식

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

수율 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

수율 43.0%

용매

THF

반응 조건

후처리

1. 1
   기타to reach room temperature
2. 2
   기타After reaching room temperature
3. 3
   workup.STIRRINGthe reaction mixture was stirred for a further 18 h
4. 4
   기타quenched by the addition of methanol (1 ml)
5. 5
   농축The resultant solution was concentrated under reduced pressure
6. 6
   기타the residue partitioned between water and DCM
7. 7
   기타The organic layer was separated
8. 8
   건조dried (over magnesium sulphate)
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The residue was purified by mass

실험 절차

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.

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