반응 #58554

반응 방정식

NaOH

AlCl3

tert-butylaminoborane

HCl

product

5-Benzyl-3b,4,5,6,7,7a-hexahydro-3-thia-5-aza-cyclopenta[α]inden-8-one

AlCl3 borane

→

subtitle compound

수율 64.0%

5-Benzyl-4,5,6,7,7a,8-hexahydro-3bH-3-thia-5-aza-cyclopenta[α]indene

수율 64.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.WAITAfter 2 hours at 0° C.
2. 2
   기타the crude reaction mixture
3. 3
   추출extracted with CH2Cl2 (3×75 ml)
4. 4
   세척The combined organic extracts were washed with brine (75 ml)
5. 5
   건조dried (MgSO4), and solvent
6. 6
   기타evaporated in vacuo
7. 7
   기타leaving the crude product that
8. 8
   기타was purified by silica-gel chromatography

실험 절차

A slurry of AlCl3 (946 mg, 7.11 mmol) in CH2Cl2 (7 ml) was treated with tert-butylaminoborane (1.24 g, 14.22 mmol) at 0° C. and stirred for 30 minutes. Next, a solution of the product from step e) (671 mg, 2.37 mmol) in CH2Cl2 (5 ml) was added dropwise to the AlCl3/borane solution. After 2 hours at 0° C., the crude reaction mixture was poured into cold 10% HCl, treated with 2 M NaOH to pH 12 and extracted with CH2Cl2 (3×75 ml). The combined organic extracts were washed with brine (75 ml), dried (MgSO4), and solvent evaporated in vacuo leaving the crude product that was purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 75% ethyl acetate) to give the subtitle compound (409 mg, 64%). MS calculated for C17H19NS+H 270, observed 270.

출처