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

HRID 992270노트

반응식

HRID 992270 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-c8a9c210ba084c37aced4ecef5bae1ad
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06468998B1

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