반응 #219807

반응 방정식

(S)-2-Methyl-propane-2-sulfinic acid ((3S)-1,3-dimethyl-pentylidene)-amide

diisopropylamine

butyllithium

Methyl acetate

→

titled compound

수율 62.1%

(3S,5S)-3,5-Dimethyl-3-((S)-2-methyl-propane-2-sulfinylamino)-heptanoic acid methyl ester

수율 62.1%

용매

THF

THF

THF

THF

반응 조건

후처리

1. 1
   기타at −78° C.
2. 2
   온도subsequently cooled down to −78° C
3. 3
   workup.STIRRINGAfter Stirring for 20 minutes
4. 4
   workup.STIRRINGthe resulting mixture was stirred at −78° C. for 20 minutes
5. 5
   workup.STIRRINGThe mixture was stirred at −78° C. overnight
6. 6
   기타The reaction was quenched by NH4Cl solution (50 mL)
7. 7
   여과The mixture was filtered
8. 8
   추출The filtrate was extracted by EtOAc (3×70 mL)
9. 9
   기타the residue was purified by a silica gel column (Hexane/EtOAc 1:1)

실험 절차

To a solution of diisopropylamine (3.1 mL, 22.2 mmol) in THF (40 mL) at −78° C. was slowly added butyllithium (14.4 mL, 1.6 M, 23 mmol). The mixture was stirred at 0° C. for 25 minutes and subsequently cooled down to −78° C. Methyl acetate (1.76 mL, 22.2 mmol) in THF (7 mL) was added. After Stirring for 20 minutes, chlorotitaniumtriisopropoxide (11 mL, 46.2 mmol) in THF (10 mL) was added and the resulting mixture was stirred at −78° C. for 20 minutes. (S)-2-Methyl-propane-2-sulfinic acid ((3S)-1,3-dimethyl-pentylidene)-amide (1.9 g, 8.9 mmol) in THF (10 mL) was added. The mixture was stirred at −78° C. overnight. The reaction was quenched by NH4Cl solution (50 mL). The mixture was filtered. The filtrate was extracted by EtOAc (3×70 mL). The EtOAc phase was reduced under reduce pressure and the residue was purified by a silica gel column (Hexane/EtOAc 1:1) to give the titled compound (1.61 g, 62% yield) as a colorless oil: 1H NMR (CDCl3) δ 3.64 (s, 3H), 2.60 (m, 2H), 1.47 (m, 2H), 1.44 (m, 1H), 1.36 (s, 3H), 1.27 (m, 2H), 1.19 (s, 9H), 0.90 (d, J=6.4 Hz, 3H), 0.81 (t, J=7.6 Hz, 3H); MS (APCI) (M+1)+ 292.2.

출처