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

HRID 1372436노트

반응식

HRID 1372436 반응식
[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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 297576-Nitroindoline

생성물 1

HCID 223825671-Benzyloxycarbonyl-2,3-dihydro-6-nitroindole수율 68%

시약·촉매·용매 2

HCID 218852-Dimethylaminopyridine촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b6e8643cc5b94eed82ef8462b4a67861
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157585B2

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