Triethylamine → (S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992288노트

반응식

HRID 992288 반응식
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.C(N(CC)CC)C.[C:21]12([C:31](Cl)=[O:32])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>CN(C=O)C>[CH2:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:31]([C:21]23[CH2:30][CH:25]4[CH2:24][CH:23]([CH2:29][CH:27]([CH2:26]4)[CH2:28]2)[CH2:22]3)=[O:32])[CH2:3]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidine

생성물 1

HCID 9884297(S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide수율 77.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S)-3-Amino-1-benzylpyrrolidine (10 g) and triethylamine (24 ml) were dissolved in DMF (100 ml). Under ice-cooling, 1-adamantanecarbonyl chloride (12.4 g) was added thereto, and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure. To the obtained residue was added ethyl acetate and the mixture was washed with saturated brine. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (chloroform:methanol=30:1). The obtained eluate was concentrated and IPE was added to the obtained residue. The precipitated crystals were collected by filtration to give (S)-N-(1-benzylpyrrolidin-3-yl)-1-adamantanecarboxamide (14.8 g), melting point 130-132° C.

후처리

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure
  3. additionTo the obtained residue was added ethyl acetate
  4. washthe mixture was washed with saturated brine
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe obtained eluate was concentrated
  7. additionIPE was added to the obtained residue
  8. filtrationThe precipitated crystals were collected by filtration

출처 및 근거

ORD 기록
ord-f50cc3d55cf34034827cb4f2a2a80aee
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06468998B1

반응 노트

불러오는 중…