반응 #70623

반응 방정식

MeOH

sodium borohydride

N-tert-butyl-4-cyano-3-methylbenzenesulfonamide

MeMgBr

→

4-(1-aminoethyl)-N-tert-butyl-3-methylbenzenesulfonamide

용매

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux overnight
3. 3
   온도After cooling
4. 4
   workup.ADDITIONwas added
5. 5
   온도warmed to room temperature
6. 6
   workup.STIRRINGstirred for 4 hours
7. 7
   기타The reaction mixture was then quenched with H2O
8. 8
   workup.STIRRINGstirred overnight
9. 9
   농축concentrated
10. 10
    기타to give a yellow solid
11. 11
    기타The solid was partitioned between EtOAc/H2O
12. 12
    기타the organic layer was separated
13. 13
    건조dried (MgSO4)
14. 14
    농축concentrated
15. 15
    기타to give a yellow oil
16. 16
    기타The oil was purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA)

실험 절차

A solution of N-tert-butyl-4-cyano-3-methylbenzenesulfonamide (0.4861 g) in THF (19 ml) at 0° C. was treated with MeMgBr (1.4 M in THF, 4.13 ml). The reaction mixture was heated at reflux overnight. After cooling, the reaction was quenched with MeOH and sodium borohydride (3 eq) was added. The mixture was stirred at 0° C. for 1 h, warmed to room temperature and stirred for 4 hours. The reaction mixture was then quenched with H2O, stirred overnight and concentrated to give a yellow solid. The solid was partitioned between EtOAc/H2O and the organic layer was separated, dried (MgSO4) and concentrated to give a yellow oil. The oil was purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA) to give 0.3403 g 4-(1-aminoethyl)-N-tert-butyl-3-methylbenzenesulfonamide as white powder after lyophilization.

출처