Isopropyl Acetate → 5-(4-tert-Butylphenyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylic Acid Ethyl Ester

HRID 1697718

반응식

HRID 1697718 반응식
[C:1]([C:5]1[CH:18]=[CH:17][C:8](/[CH:9]=[N:10]/[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br-].[Li+].C(N(CC)CC)C.[CH:28]([S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])=[CH2:29].C(OC(C)=O)(C)C>C1COCC1>[CH2:15]([O:14][C:12]([CH:11]1[CH2:29][CH:28]([S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:31])=[O:32])[CH:9]([C:8]2[CH:17]=[CH:18][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][CH:7]=2)[NH:10]1)=[O:13])[CH3:16]

참가 물질

7

반응물 5

HCID 7915Isopropyl AcetateHCID 8471TriethylamineHCID 79664Phenyl vinyl sulfoneHCID 82050Lithium BromideHCID 178472689HCID 178472689, 화합물

생성물 1

HCID 667708285-(4-tert-Butylphenyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylic Acid Ethyl Ester수율 8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (E)-ethyl 2-(4-tert-butylbenzylideneamino)acetate (226 mg, 914 umol; example 441a) in THF (5 ml) under an argon atmosphere were added lithium bromide (119 mg, 1.37 mmol), triethylamine (191 ul, 1.37 mmol) and phenyl vinyl sulfone (154 mg, 914 umol; CAS Reg. No. 5535-48-8). The mixture was stirred at ambient temperature for 20 h. iPrOAc (50 ml) and ice water (40 ml) were added and the layers were separated. The organic layer was washed with brine (40 ml), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, iPrOAc/n-heptane) to obtain the title compound (56 mg, 73 umol; 8%) as colorless solid. MS (ESI): m/z=416.2 [M+H]

후처리

  1. additionwere added
  2. customthe layers were separated
  3. washThe organic layer was washed with brine (40 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customto give a yellow oil which
  8. customwas purified by column chromatography (silica gel, iPrOAc/n-heptane)

출처 및 근거

ORD 기록
ord-4a5887a39fce47c6962960c891c32db4
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163793B2

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