Potassium Hydroxide → HCID 58065873、化合物

HRID 1752208ノート

反応式

HRID 1752208 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+].[O:24]([CH2:31][CH:32]1[CH2:34][O:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:34][CH:32]([OH:33])[CH2:31][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:6]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 31217Phenyl glycidyl etherHCID 57950382tert-Butyl 8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

生成物 1

HCID 58065873HCID 58065873、化合物収率 21%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of tert-butyl 8-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (449.7 mg, 1.28 mmol) and powdered potassium hydroxide (86.9 mg, 1.54 mmol) in acetone (4.0 ml) was stirred for 15 minutes before the addition of 2-(phenoxymethyl)oxirane (254 mg, 1.69 mmol). After 1 h the reaction was condensed, diluted with EtOAc and washed twice with water and then brine. The organic layer was then dried over Na2SO4, filtered and condensed. The crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N). Yield=21%. ESI (m/z): 546.6 (M+CHCOO−).

後処理

  1. customcondensed
  2. washwashed twice with water
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. filtrationfiltered
  5. customcondensed
  6. customThe crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N)

出典と根拠

ORDレコード
ord-ab7c1051e931418e8ff30a83c5ea515c
出典データセット
uspto-grants-2015_10
特許番号
US09162980B2

反応ノート

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