Water → HCID 18689933、化合物

HRID 1871921ノート

反応式

HRID 1871921 の反応式
[Cl-].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][C:47](=O)[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38].O>C1COCC1>[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][C:47](=[CH:12][C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:2]=2)[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:38])[CH3:39]

参加物

6

反応物 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 22241267Triphenyl[(quinolin-2-yl)methyl]phosphanium chlorideHCID 178418339Butyllithium

生成物 1

HCID 18689933HCID 18689933、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under argon, 2-quinolylmethyltriphenylphosphonium chloride (8.72 g) was dissolved in anhydrous THF (60 ml), and a 1.6N solution (15 ml) of butyllithium was added dropwise over 20 minutes under cooling on ice. The mixture was then stirred for 10 minutes at room temperature. To the mixture, an anhydrous THF (24 ml) solution of 1-tert-butoxycarbonyl-4-ketopiperidine (4.29 g) was added dropwise over 15 minutes under cooling on ice. The mixture was stirred for 30 minutes under cooling on ice and further stirred overnight at room temperature. Water (200 ml) was added to the reaction mixture, then the resultant mixture was extracted with ether. The organic phase was back-extracted with 1N hydrochloric acid, and the aqueous phase was neutralized with a saturated solution of sodium hydrogencarbonate. The resultant mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure, to thereby obtain the title compound as a solid. This solid was used for subsequent reaction without further purification.

後処理

  1. temperatureunder cooling on ice
  2. temperatureunder cooling on ice
  3. stirringThe mixture was stirred for 30 minutes
  4. temperatureunder cooling on ice and further stirred overnight at room temperature
  5. extractionthe resultant mixture was extracted with ether
  6. extractionThe organic phase was back-extracted with 1N hydrochloric acid
  7. extractionThe resultant mixture was extracted with ethyl acetate
  8. washThe organic phase was washed with saturated brine
  9. dry with materialdried over sodium sulfate anhydrate
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c7eea003885d4a6bb244f16252590299
出典データセット
uspto-grants-2000_08
特許番号
US06107308

反応ノート

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