Propargyl bromide → HCID 15086767, 화합물

HRID 1534544노트

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HRID 1534544 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 15086767HCID 15086767, 화합물

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2887ad1162ba40fba438de0193d0cc25
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05089518

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