Propylamine → N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine

HRID 37994

Reaktionsgleichung

Reaktionsgleichung von HRID 37994
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH3:5][C:6]1([CH3:13])[O:10][CH:9]([CH:11]=O)[CH2:8][O:7]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:13][C:6]1([CH3:5])[O:10][CH:9]([CH2:11][NH:4][CH2:1][CH2:2][CH3:3])[CH2:8][O:7]1

Komponenten

5

Edukt 3

HCID 7852PropylamineHCID 1107022,2-Dimethyl-1,3-dioxolane-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 57577780N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amineAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of propylamine (0.72 mL, 7.7 mmol) and 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1.0 g, 7.7 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (2.28 g, 10.8 mmol). The mixture was stirred for 1.5 h at room temperature. The reaction mixture was then quenched with sat'd aq NaHCO3 and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) to afford 1.26 g (73%) of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine.

Aufarbeitung

  1. customThe reaction mixture was then quenched with sat'd aq NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude material that
  7. customwas purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-3cf4e12ef20e427cba563ac0e925fe95
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524702B2

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