Réaction #43404

Équation de réaction

water

triethylamine

para-toluenesulphonyl chloride

(4R/S)-3-chloro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

→

product

Rendement 95.2%

[(4R/S)-(3-Chloro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)]methyl 4-methylbenzenesulfonate

Rendement 95.2%

Solvants

dichloromethane tetrahydrofuran N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Autrethe phases separated
2. 2
   LavageThe organic phase was washed with saturated aqueous sodium bicarbonate solution
3. 3
   Autrethen dried
4. 4
   Autreevaporated

Mode opératoire

A suspension of (4R/S)-3-chloro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (300 mg, 1.2 mmol) in dichloromethane/tetrahydrofuran/N,N-dimethylformamide (10 ml/10 ml/2 ml) was treated with triethylamine (0.25 ml, 1.8 mmol), para-toluenesulphonyl chloride (220 mg, 1.2 mol) and dibutyltin oxide (15 mg, 0.06 mmol). After 3 hours water was added and the phases separated. The organic phase was washed with saturated aqueous sodium bicarbonate solution then dried and evaporated affording the product (465 mg).

Source