Triethylamine → 2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-amine

HRID 1806843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1806843
O[CH2:2][CH2:3][C@@H:4]1[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5]1.CS(Cl)(=O)=O.C([N:18](CC)CC)C.[N-]=[N+]=[N-].[Na+]>ClCCl.CN(C)C=O.C(OCC)(=O)C.O=[Pt]=O>[CH3:9][C:6]1([CH3:10])[O:5][C@H:4]([CH2:3][CH2:2][NH2:18])[CH2:8][O:7]1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 11480522(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Produkt 1

HCID 282937752-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 345198Adams' catalystKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Step A In a manner similar to the method described in Example 3a Step A to C, (4R)-(−)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (Aldrich) (4.91 g, 33.6 mmol) was reacted with methanesulfonyl chloride (3.12 mL, 40.3 mmol) and triethylamine (9.34 mL, 67 mmol) in dichloromethane, then reacted with NaN3 (10.7 g, 0.16 mol) in N,N-dimethylformamide, then treated with PtO2 and H2 (50 psi) in ethyl acetate to give 2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine as a brown oil (4.4 g, 90% for three steps).

Quellen und Nachweise

ORD-Eintrag
ord-0a422cad0a334c4ea1124acbdb87778e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354444B2

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