Reaktion #12021

Reaktionsgleichung

(bromomethyl)cyclopropane

sodium bicarbonate

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

sodium hydride

→

compound

Ausbeute 67.1%

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

Ausbeute 67.1%

Lösungsmittel

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic layer was washed with brine
2. 2
   Trocknendried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was purified by chromatography on silica gel (0.032–0.063 mm) with a gradient of ethyl acetate:n-hexane (1:1 to 100:0) as eluant

Vorschrift

To a solution of 1.2 g (37.6 mmol) (4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 30 ml N,N-dimethylformamide was added 0.18 g (41.4 mmol) sodium hydride. After 30 min 0.72 ml (1.01 g, 75.2 mmol) (bromomethyl)cyclopropane was added and the reaction was stirred for 3 h. The reaction mixture was poured into 10% aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel (0.032–0.063 mm) with a gradient of ethyl acetate:n-hexane (1:1 to 100:0) as eluant to afford the compound as a light yellow oil (67.1%).

Quelle