1-Bromo-2-methylpropane → (S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamate

HRID 529563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529563
[O:1]=[C:2]1[C@@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].[CH2:19](Br)[CH:20]([CH3:22])[CH3:21].[NH4+].[Cl-]>CN(C=O)C>[CH2:19]([N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]1=[O:1])[CH:20]([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7022178(S)-tert-Butyl (2-oxoazepan-3-yl)carbamate

Produkt 1

HCID 68310529(S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 2-oxoazepan-3-ylcarbamate (116 mg, 0.510 mmol) in DMF (2 mL) at 0° C. was added sodium hydride (60% in oil, 23 mg, 0.57 mmol) in 2 portions. After stirring for 5 min, isobutyl bromide (175 mg, 1.28 mmol) was added to the reaction mixture and the mixture was stirred at rt for 20 h. Saturated aqueous NH4Cl (2 mL) was added to the mixture and crude product was extracted with methylene chloride (3 mL) and the combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified using silica gel chromatography to afford (S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamate (46.4 mg, 0.247 mmol, 49% yield). Anal. Calcd. for C15H28N2O3 m/z 284.2. found: 285.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.44 (d, J=6.64 Hz, 1H), 4.26 (t, J=9 Hz, 1H), 3.57-3.50 (m, 1H), 3.26-3.17 (m, 2H), 3.10-3.05 (m, 1H), 1.84-1.62 (m, 5H), 1.37 (s, 9H), 1.34-1.24 (m, 2H), 0.84-0.80 (m, 6H).

Aufarbeitung

  1. stirringthe mixture was stirred at rt for 20 h
  2. extractionwas extracted with methylene chloride (3 mL)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-7bb752e53f454cb3869c006670397167
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346852B2

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