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1-[4-(Bromomethyl)phenyl]-1H-pyrrole → HCID 54243183, 화합물

HRID 1600575
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HRID 1600575 반응식
[Li].C[Si]([NH-])(C)C.[CH3:7][O:8][C:9](=[O:25])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1.[N:26]1([C:31]2[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27]1>C1COCC1>[CH3:7][O:8][C:9](=[O:25])[C@:10]1([CH2:35][C:34]2[CH:33]=[CH:32][C:31]([N:26]3[CH:30]=[CH:29][CH:28]=[CH:27]3)=[CH:38][CH:37]=2)[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:24])[C:16]1[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 27954561-[4-(Bromomethyl)phenyl]-1H-pyrroleHCID 3028194LithiumHCID 53627528(Trimethylsilyl)amideHCID 53972052HCID 53972052, 화합물

생성물 1

HCID 54243183HCID 54243183, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a -78° C. solution of lithium bis(trimethylsilylamide (8 mL, 8 mmol) in THF is slowly added N-(3,5-dimethylbenzoyl)proline methyl ester (1.0 g, 3.8 mmol). After 20 minutes p-(1-pyrrolyl)-benzyl bromide (950 mg) in 5 mL of THF is added over a 5 minute period. The solution is warmed to room temperature, quenched with acetic acid and concentrated under reduced pressure. The residue is extracted with EtOAc. The organic layer is washed with NH4Cl (sat.), NaHCO3 solution, dried (MgSO4) and chromatographed on silica gel eluting with hexane/ethyl acetate (3:1) giving N-(3,5-dimethylbenzoyl)-2-[p-(1-pyrrolyl)-benzyl]-proline methyl ester.

후처리

  1. customTo a -78° C.
  2. customquenched with acetic acid
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue is extracted with EtOAc
  5. washThe organic layer is washed with NH4Cl (sat.), NaHCO3 solution
  6. dry with materialdried (MgSO4)
  7. customchromatographed on silica gel eluting with hexane/ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-e809b965ce1c4adc8fd977300b80d450
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05977075

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