Potassium Carbonate → 1-Boc-3-(3-nitro-5-trifluoromethyl-phenoxymethyl)-azetidine

HRID 889966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889966
[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][O:13]S(C)(=O)=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:18]([C:21]1[CH:22]=[C:23](O)[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)([O-:20])=[O:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(O)=O.[Na+].CCOC(C)=O>[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][O:13][C:23]2[CH:24]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Produkt 1

HCID 222494081-Boc-3-(3-nitro-5-trifluoromethyl-phenoxymethyl)-azetidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of 1-Boc-3-methylsulfonyloxymethyl-azetidine (1.47 g), 3-nitro-5-trifluoromethyl-phenol (1.15 g) and K2CO3 (1.15 g) in DMF(20 ml) at 80° C. was stirred overnight. The reaction was cooled to RT and diluted with 25 mL of sat. NaHCO3 and 50 mL of EtOAc. The organic phase was separated and washed with brine (25 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (50% EtOAc/hex).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by column chromatography (50% EtOAc/hex)

Quellen und Nachweise

ORD-Eintrag
ord-53e947a2d97749ef85c954823a04b896
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995162B2

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