반응 #69977

반응 방정식

sodium borohydride

4-oxoadamantane-1-carboxylic acid methyl ester

ammonia

→

4-aminoadamantane-1-carboxylic acid methyl ester

용매

methanol

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction medium is stirred for a further 3 h
2. 2
   농축After concentrating to dryness under reduced pressure
3. 3
   workup.ADDITIONadding water and ethyl acetate
4. 4
   추출the aqueous phase is extracted three times in ethyl acetate
5. 5
   건조dried over magnesium sulphate
6. 6
   농축concentrated to dryness
7. 7
   기타The crude product obtained
8. 8
   기타is chromatographed on silica gel, elution

실험 절차

5 g of 4-oxoadamantane-1-carboxylic acid methyl ester are placed in 26 ml of methanol under nitrogen. 86 ml of a 7N solution of ammonia in methanol are added. The reaction medium is stirred for 18 h, 4 g of sodium borohydride are then added at 0° C. and the reaction medium is stirred for a further 3 h. After concentrating to dryness under reduced pressure and adding water and ethyl acetate, the aqueous phase is extracted three times in ethyl acetate. The organic phases are combined, dried over magnesium sulphate and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of heptane/acetone/methanol/NH4OH solvent from 1/0/0 to 4/5/1/0.1. 1.5 g of 4-aminoadamantane-1-carboxylic acid methyl ester are obtained in the form of a mixture of cis/trans (1/3) isomers.

출처