Ammonium Chloride → cis-4b,5,9b,10-Tetrahydro-4b,6,7,9,9b-pentamethyl-8-methoxyindeno[1,2-b]indole

HRID 439869노트

반응식

HRID 439869 반응식
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]3[C:11]4[C:16]([CH2:17][C:7]3([CH3:18])[C:6]=2[C:5]([CH3:19])=[C:4]([O:20][CH3:21])[C:3]=1[CH3:22])=[CH:15][CH:14]=[CH:13][CH:12]=4.[CH3:23][Li].[NH4+].[Cl-]>C1COCC1.CCOCC>[CH3:23][C@@:8]12[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][C@:7]1([CH3:18])[C:6]1[C:5]([CH3:19])=[C:4]([O:20][CH3:21])[C:3]([CH3:22])=[C:2]([CH3:1])[C:10]=1[NH:9]2

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 22408484HCID 22408484, 화합물HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 57223553cis-4b,5,9b,10-Tetrahydro-4b,6,7,9,9b-pentamethyl-8-methoxyindeno[1,2-b]indole

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a cold (-80° C.) solution of 1.1 g (0.0038 mol) of 9b,10-dihydro-6,7,9,9b-tetramethyl-8-methoxyindeno[1,2-b]indole in 20 ml of dry THF was added 4 ml of 1.6M methyl lithium in ether under argon. The mixture was stirred at -78° C. for 1 hour and then at -20° C. for 1 hour. After attaining 0° C. aqueous NH4Cl and ether was added. The phases were separated, and the organic phase was washed once with water, dried (MgSO4) and evaporated. The resulting crude product was purified by chromatography on silica using ethyl acetate/isooctane (2/10) as eluant. This gave 0.3 g (25%) of the expected product. 1H NMR (CDCl3): 1.41 (3H,s), 1.43 (3H,s), 1.96 (3H,s), 2.07 (3H,s), 2.35 (3H,s), 3.0 (1H,d), 3.55 (3H,s), 3.65 (1H,d), 7.1 (3H,m), 7.25 (1H,m).

후처리

  1. waitat -20° C. for 1 hour
  2. customAfter attaining 0° C.
  3. additionwas added
  4. customThe phases were separated
  5. washthe organic phase was washed once with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe resulting crude product was purified by chromatography on silica

출처 및 근거

ORD 기록
ord-b21f90eb529046a490fea73bfa45df42
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516788

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