Reaction #10208

Reaction equation

Sodium

methanol

6-chloro-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-carboxylic acid tert-butyl ester

methanol

→

6-Methoxy-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-carboxylic acid tert-butyl ester

Conditions

Workup

1. 1
   Temperatureto reflux for 18 hours
2. 2
   TemperatureThe mixture was cooled
3. 3
   Concentrationconcentrated
4. 4
   workup.ADDITIONtreated with H2O
5. 5
   Extractionextracted with CH2Cl2
6. 6
   WashThe organic layer was washed with saturated NaCl solution
7. 7
   Filtrationfiltered through a cotton plug
8. 8
   Concentrationthen concentrated to an oil (165 mg)

Procedure

Sodium metal (˜12 mg) was dissolved in methanol (1 mL) under nitrogen with stirring and treated with a solution of 6-chloro-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-carboxylic acid tert-butyl ester (118 mg, 0.33 mmol) in methanol (3 mL) and brought to reflux for 18 hours. The mixture was cooled, concentrated, treated with H2O and extracted with CH2Cl2. The organic layer was washed with saturated NaCl solution and filtered through a cotton plug then concentrated to an oil (165 mg). (TLC: 5% methanol/CH2Cl2 Rf 0.55).

Source