Water → Tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate

HRID 1809634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809634
[N:1]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:6][CH2:5][CH:4]([C:8](OCC)=[O:9])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:9][CH2:8][CH:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 667519511-tert-Butyl 4-ethyl azepane-1,4-dicarboxylate

Produkt 1

HCID 68708706Tert-butyl 4-(hydroxymethyl)azepane-1-carboxylateAusbeute 101,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-tert-Butyl 4-ethyl azepane-1,4-dicarboxylate (3.3 g, 12 mmol, US Publication No. 2006/229289) was dissolved in THF (100 mL) and cooled in an ice bath. LiAlH4 (12 mL, 12 mmol) was added slowly and stirred for 30 minutes. Water (˜3 mL) was added slowly, followed by Na2SO4. The reaction was filtered and concentrated to afford crude tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate (2.8 g, 100%).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b9a0e17844934d85a86779cdebcd2eea
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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