Hydrazine hydrate (1:1) → (S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992270ノート

反応式

HRID 992270 の反応式
C([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)=[O:15])[CH2:9]1)C1C=CC=CC=1.O.NN>C(O)C.[C].[Pd]>[NH:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)=[O:15])[CH2:9]1

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 9884297(S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide

生成物 1

HCID 49760538(S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide収率 93.5%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

(S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide (10.5 g, described in Example 13) was dissolved in ethanol (100 ml), and 10% palladium-carbon (5 g) was added thereto. The mixture was stirred at room temperature, and to the reaction mixture was added hydrazine monohydrate (1.5 ml). The mixture was stirred under heating for 1 hour. The reaction mixture was cooled to room temperature, and 10% palladium-carbon was filtered off with celite. The filtrate was concentrated, and IPE (isopropyl ether) was added to the obtained residue. The precipitated crystals were collected by filtration to give (S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide (7.2 g), melting point 186-188° C.

後処理

  1. stirringThe mixture was stirred
  2. temperatureunder heating for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtration10% palladium-carbon was filtered off with celite
  5. concentrationThe filtrate was concentrated
  6. additionIPE (isopropyl ether) was added to the obtained residue
  7. filtrationThe precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-c8a9c210ba084c37aced4ecef5bae1ad
出典データセット
uspto-grants-2002_10
特許番号
US06468998B1

反応ノート

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