Pyridiniumtribromide → (2S,4S)-2-(2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

HRID 1431842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431842
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:6]([C:16]([O:18][CH2:19][C:20](=[O:40])[C:21]2[CH:22]=[CH:23][C:24]3[C:33]4[CH:32]=[C:31]5[CH2:34][CH2:35][CH2:36][C:37](=[O:38])[C:30]5=[CH:29][C:28]=4[O:27][CH2:26][C:25]=3[CH:39]=2)=[O:17])[CH2:5]1.[Br-:41].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.CO>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[C@H:6]([C:16]([O:18][CH2:19][C:20]([C:21]2[CH:22]=[CH:23][C:24]3[C:33]4[CH:32]=[C:31]5[CH2:34][CH2:35][CH:36]([Br:41])[C:37](=[O:38])[C:30]5=[CH:29][C:28]=4[O:27][CH2:26][C:25]=3[CH:39]=2)=[O:40])=[O:17])[CH2:5]1

Komponenten

5

Edukt 2

HCID 21124087PyridiniumtribromideHCID 86717147(2S, 4S)-1-tert-butyl 2-(2-oxo-2-(8-oxo-8,9, 10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)ethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 69675164(2S,4S)-2-(2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(2S,4S)-1-tert-Butyl 2-(2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)ethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate (7.66 g, 13.9 mmol) was dissolved in a solution of DCM (100 mL) and MeOH (40 mL), then treated with pyridinium tribromide (4.90 g, 15.3 mmol). After stirring at RT for 1.75 h, the reaction mixture was diluted with DCM and washed successively with 10% HCl, saturated aqueous NaHCO3 and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure and the crude material was carried on without further purification.

Aufarbeitung

  1. washwashed successively with 10% HCl, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customthe crude material was carried on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-1853926f27894a2c9af5f1fa7c3b2a71
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940718B2

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