Conversion of Alcohols into Primary Amines, a New Mitsunobu Version of Gabriel-type Synthesis

✍ Scribed by ??lusarska, Elżbieta ;Zwierzak, Andrzej

• Book ID: 102365505
• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: English
• Weight: 218 KB
• Volume: 1986
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198619860221

✦ Synopsis

Umwandlung von Alkoholen in primare Amine, eine neue Mitsunobu-Version der Gabriel-Sy nthese

Primare und sekundare Alkohole liefern die entsprechenden Amin-hydrochloride 3 mit guten Ausbeuten (60-85%), wenn sie unter milden Bedingungen mit N-(Diethoxyphosphory1)carbamidsaure-tert-butylester (1) in Gegenwart von Azodicarbonsaure-diethylester1Triphenylphosphan umgesetzt und danach die entstandenen N-Alkyl-N-(diethoxyphosphory1)carbamidsaureester 2 mit gasformigem HCI gespalten werden. Die Stereochemie dieser Reaktion wird untersucht.

Recently tert-butyl N-(diethoxyphosphory1)carbamidate (1) was found to be a versatile reagent in the Gabriel-type synthesis of primary amines from the respective alkyl bromides').

We have now extended the applicability of our reagent to direct transformations of primary

Experimental

Melting points were determined in capillary tubes and are uncorrected. -'H NMR spectra were obtained at 80 MHz with a Tesla BS 487C spectrometer. -31P NMR spectra were recorded at 36.43 MHz with a Bruker HFX 90 spectrometer.