Реакция #5638

Уравнение реакции

2,2,2-trichloroethylchloroformate

product

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

triethylamine

→

title compound

Выход 78.1%

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

Выход 78.1%

Растворители

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   Температураwarmed to room temperature
2. 2
   ПромывкаThe reaction mixture was washed with saturated aq. NaHCO3 solution (10 mL)
3. 3
   ЭкстракцияThe aqueous phase was extracted with CH2Cl2 (10 mL)
4. 4
   СушкаThe combined organic extracts were dried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe residue was purified by chromatography (silica gel, 10:1 heptane/ethyl acetate)

Методика

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.

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