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2-Nitrobenzaldehyde → benzyl (S)-4-[2-(2-nitrobenzylamino)-1-propoxy]benzoate

HRID 350565
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 350565
[NH2:1][C@@H:2]([CH3:21])[CH2:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:7][CH:6]=1.[N+:22]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=O)([O-:24])=[O:23].[BH3-]C#N.[Na+]>CO.CC(O)=O>[N+:22]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27][NH:1][C@@H:2]([CH3:21])[CH2:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[CH:7][CH:6]=1)([O-:24])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 111012-NitrobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86587801benzyl (S)-4-(2-amino-1-propoxy)benzoate

Produkt 1

HCID 86587803benzyl (S)-4-[2-(2-nitrobenzylamino)-1-propoxy]benzoateAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

To a stirred and cooled (0° C.) solution of benzyl (S)-4-(2-amino-1-propoxy)benzoate (1.50 g, 5.26 mmol) and 2-nitrobenzaldehyde (0.87 g, 5.76 mmol) in MeOH—AcOH (16 mL, 15:1, v/v) was added NaBH3CN (1.65 g, 26.3 mmol), and the resulting mixture was stirred at room temp overnight. The mixture was quenched by sat. NaHCO3 and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3 to 5% MeOH in CHCl3 as eluent to give 931 mg (42%) benzyl (S)-4-[2-(2-nitrobenzylamino)-1-propoxy]benzoate as a yellow oil. 1H-NMR (CDCl3) δ 1.21 (d, 3 H, J=6.4 Hz), 3.13–3.18 (m, 1 H), 3.88–3.97 (m, 2 H), 4.06–4.20 (m, 2 H), 5.34 (s, 2 H), 6.89–6.94 (m, 2 H), 7.29–7.65 (m, 8 H), 7.94–8.03 (m, 3 H); MS (FAB) m/z 421 (M++1).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temp overnight
  2. customThe mixture was quenched by sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica-gel with CHCl3 to 5% MeOH in CHCl3 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1a651a828d3a4a53ad39714e90527d69
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07179819B2

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