Reaction #5637

Reaction equation

ethyl chloroformate

product

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

triethylamine

→

title compound

Yield 98.0%

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

Yield 98.0%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   Washwashed with water
2. 2
   ExtractionThe aqueous phase was extracted with CH2Cl2 (3×20 mL)
3. 3
   Dryingthe combined organic extracts were dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate)

Procedure

A solution of the product from Example 9 (1.05 g, 4.28 mmol) and triethylamine (0.44 g, 4.35 mmol) in 10 mL of CH2Cl2 was cooled to 0° C. and ethyl chloroformate (0.47 g, 4.33 mmol) in 5 mL CH2Cl2 was added dropwise. The reaction was warmed to room temperature and washed with water. The aqueous phase was extracted with CH2Cl2 (3×20 mL) and the combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate) to give the title compound (1.33 g, 98%) as an oil.

Source