تفاعل #69977

معادلة التفاعل

sodium borohydride

4-oxoadamantane-1-carboxylic acid methyl ester

ammonia

→

4-aminoadamantane-1-carboxylic acid methyl ester

المذيبات

methanol

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر