반응 #1547381

반응 방정식

water

product

Ethyl (±)-[2-(3',4'-dihydro-2'-hydroxyspiro-[cyclopentane-1,1'(2'H)-napthalen]-2'-yl)ethyl]-carbamate

sulfuric acid

acetic acid

→

title compound

수율 59.0%

Ethyl (±)-2,3,4,5-tetrahydro-3a,9b-butano-1H-benz[g]indole-1-carboxylate

수율 59.0%

반응 조건

후처리

1. 1
   추출the resulting mixture was extracted with CH2Cl2 (4×30 mL)
2. 2
   건조The combined organic extracts were dried (MgSO4)
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (100 mL
6. 6
   세척washed with saturated aq. bicarbonate solution (30 mL)
7. 7
   건조The organic phase was dried (MgSO4)
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타The residue was purified by chromatography (silica gel, 9:1 heptane/ethyl acetate)

실험 절차

A solution of the product from Example 13 (1.68 g, 5.29 mmol) in 15 mL of 3:1 acetic acid/concentrated sulfuric acid (v/v) was stirred at room temperature for 18 hours. The reaction mixture was poured into water (50 mL) and the resulting mixture was extracted with CH2Cl2 (4×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was dissolved in CH2Cl2 (100 mL and washed with saturated aq. bicarbonate solution (30 mL). The organic phase was dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (silica gel, 9:1 heptane/ethyl acetate) to give the title compound (0.94 g, 59%) as a white solid mp 67°-69° C.

출처