Triethylamine → 1-Benzyloxycarbonyl-2,3-dihydro-6-nitroindole

HRID 1372436ノート

反応式

HRID 1372436 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>ClCCl.CN(C1C=CC=CN=1)C>[CH2:24]([O:23][C:21]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 297576-Nitroindoline

生成物 1

HCID 223825671-Benzyloxycarbonyl-2,3-dihydro-6-nitroindole収率 68%

試薬・触媒・溶媒 2

HCID 218852-Dimethylaminopyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 6-nitroindoline (10.0 g, 0.061 mol), triethylamine (22.7 mL, 0.16 mol) and dimethylaminopyridine (50 mg, cat.) in dichloromethane (130 mL) was stirred at 0° C. and benzyl chloroformate (18 mL, 0.12 mol) was added slowly. The mixture was allowed to warm to room temperature overnight. The mixture was washed with water (50 mL), 5% aqueous HCl (100 mL), saturated aqueous NaHCO3 (50 mL) and water (50 mL). The dichloromethane was dried (MgSO4) and evaporated under reduced pressure to give an orange solid. This was triturated in diethyl ether (150 ml) to give a yellow solid (12.34 g, 68%).

後処理

  1. washThe mixture was washed with water (50 mL), 5% aqueous HCl (100 mL), saturated aqueous NaHCO3 (50 mL) and water (50 mL)
  2. dry with materialThe dichloromethane was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto give an orange solid
  5. customThis was triturated in diethyl ether (150 ml)

出典と根拠

ORDレコード
ord-b6e8643cc5b94eed82ef8462b4a67861
出典データセット
uspto-grants-2007_01
特許番号
US07157585B2

反応ノート

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