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

HRID 439869ノート

反応式

HRID 439869 の反応式
[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

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 22408484HCID 22408484、化合物HCID 178418348HCID 178418348、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b21f90eb529046a490fea73bfa45df42
出典データセット
uspto-grants-1996_05
特許番号
US05516788

反応ノート

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