반응 #1359294

반응 방정식

(R)-6-chloro-4,7-dimethyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

sodium cyanoborohydride

→

product

수율 80.3%

(4R,9aR)-6-Chloro-4,7-dimethyl-3,4,9,9a-tetrahydro-1 H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

수율 80.3%

용매

acetic acid

반응 조건

후처리

1. 1
   기타After 2 h the volatile components were removed at a rotary evaporator
2. 2
   workup.ADDITIONtreated with 32% aqueous sodium hydroxide solution until a pH of 11
3. 3
   기타was obtained
4. 4
   추출The aqueous phase was extracted twice with ethyl acetate
5. 5
   세척the combined organic layers were washed with brine
6. 6
   건조dried over magnesium sulfate
7. 7
   기타evaporated
8. 8
   기타The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:7) as eluant

실험 절차

To a solution of 0.26 g (0.77 mmol) (R)-6-chloro-4,7-dimethyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 5 mL acetic acid was added 0.24 g (3.87 mmol) sodium cyanoborohydride. After 2 h the volatile components were removed at a rotary evaporator and the residue was taken up in ethyl acetate and treated with 32% aqueous sodium hydroxide solution until a pH of 11 was obtained. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:7) as eluant to give the product as a colourless oil (80.3%).

출처