Réaction #5638

Équation de réaction

2,2,2-trichloroethylchloroformate

product

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

triethylamine

→

title compound

Rendement 78.1%

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

Rendement 78.1%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Températurewarmed to room temperature
2. 2
   LavageThe reaction mixture was washed with saturated aq. NaHCO3 solution (10 mL)
3. 3
   ExtractionThe aqueous phase was extracted with CH2Cl2 (10 mL)
4. 4
   SéchageThe combined organic extracts were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe residue was purified by chromatography (silica gel, 10:1 heptane/ethyl acetate)

Mode opératoire

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.

Source