Reaktion #12017

Reaktionsgleichung

methyl iodide

(4R,9aR)-6-(3-hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

sodium hydride

water

methyl iodide

→

desired compound

Ausbeute 73.9%

(4R,9aR)-6-(3-Methoxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Ausbeute 73.9%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe cooling bath was removed
2. 2
   Extraktionwas extracted three times with ethyl acetate
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated on a rotary evaporator
7. 7
   SonstigeThe residue was purified by chromatography on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:4) as eluant

Vorschrift

A solution of 160.0 mg (0.46 mmol) (4R,9aR)-6-(3-hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 4 ml tetrahydrofuran was cooled to 0 deg C. and treated with 24.0 mg (0.51 mmol, 60% dispersion in mineral oil) sodium hydride. After 30 min 32 μl (0.51 mmol) methyl iodide was added and the cooling bath was removed. After 6 h another 0.64 μl (1.02 mmol) methyl iodide was added and the reaction was stirred overnight. The reaction mixture was poured into water and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The residue was purified by chromatography on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:4) as eluant to afford the desired compound as a colorless oil (73.9%).

Quelle