반응 #5638

반응 방정식

2,2,2-trichloroethylchloroformate

product

(+/-)-2'-(2-Aminoethyl)-3',4'-dihydrospiro[cyclopentane-1,1'(2'H)-napthalen]-2'-ol

triethylamine

→

title compound

수율 78.1%

2,2,2-Trichloroethyl (+/-)-[2-(3',4'-dihydro-2'-hydroxyspiro[cyclopentane-1,1'(2'H)-naphthalen]-2'-yl)ethyl]carbamate

수율 78.1%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   온도warmed to room temperature
2. 2
   세척The reaction mixture was washed with saturated aq. NaHCO3 solution (10 mL)
3. 3
   추출The aqueous phase was extracted with CH2Cl2 (10 mL)
4. 4
   건조The combined organic extracts were dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by chromatography (silica gel, 10:1 heptane/ethyl acetate)

실험 절차

A solution of the product from Example 9 (0.88 g, 3.59 mmol) and triethylamine (0.40 g, 3.78 mmol) in 10 mL of CH2Cl2 was cooled to 0° C. and treated dropwise with 2,2,2-trichloroethylchloroformate (0.80 g, 3.78 mmol) in 2 mL CH2Cl2. The resulting solution was stirred at 0° C. for 30 minutes and warmed to room temperature. The reaction mixture was washed with saturated aq. NaHCO3 solution (10 mL). The aqueous phase was extracted with CH2Cl2 (10 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (silica gel, 10:1 heptane/ethyl acetate) to give the title compound (1.18 g, 78%) as a viscous oil.

출처