Reaktion #1018930

ord-2fd31e5ecc904a5ea0b2df79d4deaa57

Reaktionsgleichung

CC(=O)Oc1ccc2c(Br)c([C@@H](COC(=O)C(C)(C)C)OC(C)(C)C)c(C)cc2n1
(S)-2-(2-acetoxy-5-bromo-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate
CN
methylamine
→
Cc1cc2[nH]c(=O)ccc2c(Br)c1[C@@H](COC(=O)C(C)(C)C)OC(C)(C)C
(S)-2-(5-bromo-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyethyl pivalate
Ausbeute 57.3%

Edukte

CC(=O)Oc1ccc2c(Br)c([C@@H](COC(=O)C(C)(C)C)OC(C)(C)C)c(C)cc2n1
(S)-2-(2-acetoxy-5-bromo-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate
CN
methylamine

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Temperatur
78°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenConcentration and purification

Vorschrift

To the solution of (S)-2-(2-acetoxy-5-bromo-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate (130 mg) in ethanol (7.5 mL) was added aqueous methylamine solution (0.5 mL, 50%). The mixture was heated at 78° C. for 80 min. Concentration and purification gave (S)-2-(5-bromo-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyethyl pivalate (68 mg). LCMS-ESI+ (m/z): 438.2, 440.2 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09296758B2uspto-grants-2016_03