Reaction #5638

Reaction equation

2,2,2-trichloroethylchloroformate

product

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

triethylamine

→

title compound

Yield 78.1%

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

Yield 78.1%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

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

Procedure

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