Methanol → tert-Butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamate

HRID 424479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424479
[CH2:1]([N:3]([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][O:17][C:16]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:15]1=2)=O)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].B.C1COCC1.CO>C1COCC1>[CH2:1]([N:3]([CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][O:17][C:16]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:15]1=2)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:7])[CH3:8])[CH3:2]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 59144071tert-butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)-2-oxoethyl)carbamate

Produkt 1

HCID 59144101tert-Butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A yellow solution of tert-butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)-2-oxoethyl)carbamate (8.7 g, 23.8 mmol) in anhydrous THF (50 mL) under positive argon pressure was treated with borane-THF complex (1M in THF, 47.6 mL, 47.6 mmol) to give an orange solution. The mixture was refluxed for 20 minutes. It was then cooled in an ice bath and treated dropwise with MeOH (100 mL). The solution stirred for half an hour at room temperature, and the reaction was then concentrated. The residue was subjected to flash chromatography on silica gel using 1:9 EtOAc:hexanes to give an orange solid (7.5 g, 91%). 1H-NMR (DMSO-d6) δ 7.72 (dd, J=2.7, 9.0 Hz, 1H), 7.49-7.47 (m, 1H), 6.85-6.83 (m, 1H), 4.18 (t, J=4.2 Hz, 2H), 3.59-3.53 (m, 2H), 3.37-3.36 (m, 2H), 3.20-3.18 (m, 2H), 1.47 (s, 2H), 1.30 (br s, 9H), 1.02 (t, J=6.9 Hz, 3H); ESI-MS (m/z, %): 374 (MNa+, 86), 352 (MH+, 7.8), 296 (100), 252 (87).

Aufarbeitung

  1. customto give an orange solution
  2. temperatureThe mixture was refluxed for 20 minutes
  3. temperatureIt was then cooled in an ice bath
  4. concentrationthe reaction was then concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e0b6efdf35ae4690a91fc7bcf3cd1197
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106043B2

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