Lithium diisopropylamide → HCID 86585015, 화합물

HRID 1738894노트

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HRID 1738894 반응식
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[C:28]1([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([CH:41]=[CH:42][CH:43]=[O:44])[CH2:37][CH2:36]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1.C1CCCCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[CH:12]=[C:11]2[C:42](=[CH:41][CH:38]2[CH2:37][CH2:36][N:35]([CH2:34][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:40][CH2:39]2)[CH2:43][OH:44])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 2724682Lithium diisopropylamideHCID 14197466HCID 14197466, 화합물HCID 54371753HCID 54371753, 화합물

생성물 1

HCID 86585015HCID 86585015, 화합물수율 102.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

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온도
-78 °C

실험 절차

A solution of N-phenylsulfonyl-6-methyl indole (1.18 g, 4.34 mmol) in 30 ml of dry THF was cooled to -78° C. and treated with 3.5 ml (5.2 mmol) of 1.5 M lithium diisopropylamide in cyclohexane at -78° C. After stirring at -78° C. for 1 hour, a solution of 3-[1-(phenylmethyl)-4-piperidinyl]-2-propenal (1.0 g, 4.36 mmol) in 5 ml of dry THF was added at -78° C. and stirred at that temperature for 40 minutes. The mixture was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give 2.23 g of an orange oil. The oil was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give 1.0 g of the title compound as a yellow oil.

후처리

  1. stirringstirred at that temperature for 40 minutes
  2. customThe mixture was quenched with water
  3. extractionextracted with chloroform
  4. customThe organic layer was dried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5f49b9fb44bf489ca88e35f5e333d125
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965574

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