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Hexane → (3R)-5-Oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917359
ノート
印刷プレビュー

反応式

HRID 1917359 の反応式
[CH2:1]([Li])CCC.CCCCCC.[C:12]([O:16][C:17]([C@@:19]1([CH:33]=O)[CH2:23][C:22](=[O:24])[N:21]([C@@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:26])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:12]([O:16][C:17]([C@@:19]1([CH:33]=[CH2:1])[CH2:23][C:22](=[O:24])[N:21]([C@@H:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH3:26])[CH2:20]1)=[O:18])([CH3:14])([CH3:13])[CH3:15]
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

7

反応物 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 86664650(3S)-3-Formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

生成物 1

HCID 67490859(3R)-5-Oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 74505
Methyltriphenyliphosphonium bromide
触媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Methyltriphenylphosphonium bromide (187.4 mg, 0.52 mmol) was dissolved in tetrahydrofuran. A 2.62 M solution of n-butyllithium in hexane (0.16 mL, 0.42 mmol) was added dropwise in a nitrogen atmosphere at −78° C., and the mixture was stirred for one hour. After heating to 0° C., a solution of (3S)-3-formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (111 mg, 0.35 mmol) in tetrahydrofuran was added dropwise, and the mixture was stirred for one hour. A saturated ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (25% ethyl acetate/hexane) to give 54 mg of the title compound as a yellow oil.

後処理

  1. stirringthe mixture was stirred for one hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-bc8c38d1fe474726a753a4127681b2a4
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08618094B2

反応ノート

読み込み中…

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