Propargyl bromide → HCID 15086767、化合物

HRID 1534544ノート

反応式

HRID 1534544 の反応式
[CH3:1][C:2]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][NH:9][C:8]1=[O:12])([CH3:4])[CH3:3].[H-].[Na+].[CH2:17](Br)[C:18]#[CH:19]>O1CCCC1.C1(C)C=CC=CC=1.ClCCl>[CH3:4][C:2]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH2:19][C:18]#[CH:17])[C:8]1=[O:12])([CH3:1])[CH3:3]

参加物

7

反応物 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 10584804(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

生成物 1

HCID 15086767HCID 15086767、化合物

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

In one portion, 11.6 g of (S)-3-[[(1,1-dimethyl-ethyl)dimethylsilyl]oxy]-2-pyrrolidinone was added to a suspension of 2.35 g of 60% sodium hydride in mineral oil in 400 ml of tetrahydrofuran which was cooled to 0° C. The resulting solution was stirred at room temperature until solution was complete, then recooled to 0° C. An 80% solution of propargyl bromide in toluene (8.5 ml) was added and the resulting solution was stirred overnight. The solution was diluted with dichloromethane washed with water, dried and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone, [α]D26 =-44° (dichloromethane); mp 35°-36° C.

後処理

  1. customrecooled to 0° C
  2. stirringthe resulting solution was stirred overnight
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (silica gel)

出典と根拠

ORDレコード
ord-2887ad1162ba40fba438de0193d0cc25
出典データセット
uspto-grants-1992_02
特許番号
US05089518

反応ノート

読み込み中…