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

HRID 1372436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372436
[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

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 297576-Nitroindoline

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 218852-DimethylaminopyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b6e8643cc5b94eed82ef8462b4a67861
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157585B2

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