Ammonia → Methyl 4-aminoadamantane-1-carboxylate

HRID 41699

反応式

HRID 41699 の反応式
[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([C:8]3=O)[CH2:6]1)[CH2:12]2)=[O:4].[NH3:16].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH:8]3[NH2:16])[CH2:6]1)[CH2:12]2)=[O:4]

参加物

5

反応物 3

HCID 222AmmoniaHCID 4078246Methyl 4-oxoadamantane-1-carboxylateHCID 4311764Sodium borohydride

生成物 1

HCID 57425932Methyl 4-aminoadamantane-1-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  1. stirringthe reaction medium is stirred for a further 3 h
  2. concentrationAfter concentrating to dryness under reduced pressure
  3. additionadding water and ethyl acetate
  4. extractionthe aqueous phase is extracted three times in ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness
  7. customThe crude product obtained
  8. customis chromatographed on silica gel, elution

出典と根拠

ORDレコード
ord-f529236978c34c48bab4f27e15756ed0
出典データセット
uspto-grants-2013_09
特許番号
US08530657B2

関連ノート

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