Reacción #2457464

Ecuación de reacción

N-methylmorpholine oxide monohydrate

[1-allyl-4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclohexyl]-carbamic acid tert-butyl ester

[1-Allyl-4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclohexyl]-carbamic acid tert-butyl ester

water

→

[4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-1-(2,3-dihydroxy-propyl)-cyclohexyl]-carbamic acid tert-butyl ester

[4-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-1-(2,3-dihydroxy-propyl)-cyclohexyl]-carbamic acid tert-butyl ester

Disolventes

tert-butanol

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was then quenched by addition of saturated aqueous sodium bisulfite
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   Secadodried over magnesium sulfate
4. 4
   Concentraciónconcentrated

Procedimiento

A solution of 100 mg (0.19 mmol) of [1-allyl-4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclohexyl]-carbamic acid tert-butyl ester (52) in a mixture of 250 μL of water and 500 μL of acetone was treated with 36.2 mg (0.27 mmol) N-methylmorpholine oxide monohydrate and 24.0 μL (1.91 μmol) of a 2.5% solution of osmium tetroxide in tert-butanol. The mixture was stirred at room temperature until complete conversion was indicated by LCMS. The reaction was then quenched by addition of saturated aqueous sodium bisulfite, extracted with ethyl acetate, dried over magnesium sulfate and concentrated. 68 mg of crude [4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-1-(2,3-dihydroxy-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (56) could be isolated as mixture of stereoisomers. Rt=1.92 min (Method C). Detected mass: 557.3 (M+H+).

Fuente