1,4-Diiodobutane → HCID 18430942, 화합물

HRID 1278623노트

반응식

HRID 1278623 반응식
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(P(N(C)C)(N(C)C)=O)C.[I:41][CH2:42][CH2:43][CH2:44][CH2:45]I>O1CCCC1>[CH2:9]([N:16]1[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH:24]([CH2:45][CH2:44][CH2:43][CH2:42][I:41])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 123371,4-DiiodobutaneHCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 18430976Ethyl 4-(phenylmethyl)-1-piperazinebutanoate

생성물 1

HCID 18430942HCID 18430942, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-50 °C

실험 절차

To a stirred solution of lithium diisopropylamide (2 M, 32.0 ml, 6.36 mmol) in tetrahydrofuran (420 ml) was added ethyl 4-(4-benzyl-1-piperazinyl)-butanoate (6.47 g, 21.2 mmol) (Preparation 1) at −78° C. and the mixture was stirred for 1 h at the same temperature. To this mixture was added HMPA (19.4 ml) and the resultant mixture was added to a solution of 1,4-diiodobutane (13.2 g, 4.25 mmol) in tetrahydrofuran (22 ml) at −78° C. After 1 h, the temperature was raised to −50° C. and the mixture was stirred for 1 hour. The reaction was quenched by adding AcOH (0.230 ml). After the mixture was basified with aq. saturated NaHCO3, then the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 200-350 mesh/500 g/hexane:ethyl acetate=2:1) to provide a yellow oil (6.3 g/63%).

후처리

  1. waitAfter 1 h
  2. stirringthe mixture was stirred for 1 hour
  3. customThe reaction was quenched
  4. additionby adding AcOH (0.230 ml)
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/500 g/hexane:ethyl acetate=2:1)
  11. customto provide a yellow oil (6.3 g/63%)

출처 및 근거

ORD 기록
ord-2f22f2a192634bd4a625a038efe32f5b
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06444677B2

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