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Tributylvinyltin → HCID 90449481, 화합물

HRID 1411307
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HRID 1411307 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]([O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[O:23])[C:5]2=[CH:6][CH:7]=1.[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC.[Cl-].[Li+]>O1CCCC1>[CH:31]([C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]([O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])=[O:23])[C:5]2=[CH:6][CH:7]=1)=[CH2:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 90449581HCID 90449581, 화합물

생성물 1

HCID 90449481HCID 90449481, 화합물수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (1.00 g, 2.01 mmol) obtained in Step 2 of Example 383 was dissolved in tetrahydrofuran (20 mL). Thereafter, tributyl(vinyl)tin (1.40 mL, 4.79 mmol), tetrakistriphenylphosphine palladium (240 mg, 0.21 mmol), and lithium chloride (260 mg, 6.13 mmol) were added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred for 21 hours while heating under reflux. Thereafter, the reaction solution was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-vinylspiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (723 mg, 81%) in the form of a light yellow solid.

후처리

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customThereafter, the reaction solution was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-9dcfa22cf61b40bf9b2b26da4f617735
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921576B2

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