Diisopropylethylamine → 1-Methanesulfonyl-5-chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]

HRID 83985

반응식

HRID 83985 반응식
[CH3:1][S:2]([N:5]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:7]2([CH2:11][CH2:10][NH:9][CH2:8]2)[CH2:6]1)(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[Cl:28][C:29]1[CH:38]=[CH:37][C:32]([CH:33]=[CH:34][CH2:35]Cl)=[CH:31][CH:30]=1>C(#N)C.C(OCC)(=O)C>[CH3:1][S:2]([N:5]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:7]2([CH2:11][CH2:10][N:9]([CH2:35]/[CH:34]=[CH:33]/[C:32]3[CH:37]=[CH:38][C:29]([Cl:28])=[CH:30][CH:31]=3)[CH2:8]2)[CH2:6]1)(=[O:4])=[O:3]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 53728250p-Chlorocinnamyl chlorideHCID 581373391-Methanesulfonyl-5-chloro-spiro[indoline-3,3'-pyrrolidine]

생성물 1

HCID 689242391-Methanesulfonyl-5-chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]수율 45.8%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-methanesulfonyl-5-chloro-spiro[indoline-3,3′-pyrrolidine] (725 mg) in acetonitrile (40 ml) were added diisopropylethylamine (0.66 ml) and 4-chloro-cinnamyl chloride (467 mg). The resulting solution was stirred at room temperature for 12 hours, diluted with ethyl acetate, washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4) to afford 1-methanesulfonyl-5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (500 mg) which was characterised by its mass and NMR spectra. MS (ES+) 437/439 (M+H+).

후처리

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4)

출처 및 근거

ORD 기록
ord-f5ab99287f9542cdba20a7f4ba0be9a6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846907B2

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