1,4-Dibromobutane → 1-(4-Bromo-2-tert-butyl-phenyl)-pyrrolidine

HRID 1158168노트

반응식

HRID 1158168 반응식
[H-].[Na+].[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19]Br.[Cl-].[NH4+]>O1CCCC1.CS(C)=O>[Br:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

참가 물질

7

반응물 4

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 119590004-bromo-2-tert-butylphenylamine

생성물 1

HCID 666722611-(4-Bromo-2-tert-butyl-phenyl)-pyrrolidine수율 52%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

실험 절차

5.7 g (0.14 mol) of sodium hydride are suspended in 200 mL of tetrahydrofuran. 10 g (44 mmol) of 4-bromo-2-tert-butylaniline are added, along with 200 mL of dimethyl sulfoxide, added slowly. The mixture turns blue and, after 30 minutes, 13 mL (0.14 mol) of 1,4-dibromobutane are added and the reaction medium is stirred at room temperature for 13 hours. The reaction medium is then poured into saturated ammonium chloride solution and extracted with ethyl acetate, and the organic phase is then washed twice with water, dried and then concentrated to dryness. The residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate). 6.4 g of 1-(4-bromo-2-tert-butylphenyl)pyrrolidine are obtained (yield=52%) in the form of a thick yellow oil.

후처리

  1. additionadded slowly
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is then washed twice with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-242455e74f32427089eca1c5b16b0d2f
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807708B2

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