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Phenethyl bromide → (S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992277
ノート
印刷プレビュー

反応式

HRID 992277 の反応式
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)=[O:8])[CH2:2]1.Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:22]1([CH2:21][CH2:20][N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]34[CH2:18][CH:13]5[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]5)[CH2:10]3)[CH2:16]4)=[O:8])[CH2:2]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 49760538(S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide

生成物 1

HCID 9841449(S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide収率 77.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

(S)-N-(Pyrrolidin-3-yl)-1-adamantanecarboxamide (3.9 g) and 2-bromoethylbenzene (2.9 g) were dissolved in DMF, and potassium carbonate was added. The mixture was stirred under heating at 70° C. for 5 hours, and after the completion of the reaction, the solvent was evaporated under reduced pressure. Ethyl acetate was added to the obtained residue 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. The precipitated crystals were collected by filtration to give (S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide (4.3 g), melting point 119-121° C.

後処理

  1. customafter the completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. additionEthyl acetate was added to the obtained residue
  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
  8. filtrationThe precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-b412e57ab30f49e2bcc55d8f0244a90a
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06468998B1

反応ノート

読み込み中…

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