Invention Grant
- Patent Title: Synthesis of amides and amines from aldehydes or ketones by heterogeneous metal catalysis
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Application No.: US15536295Application Date: 2015-12-15
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Publication No.: US10308588B2Publication Date: 2019-06-04
- Inventor: Armando Córdova , Carlos Palo-Nieto , Samson Afewerki
- Applicant: ORGANOFUEL SWEDEN AB
- Applicant Address: SE Sundsvall
- Assignee: ORGANOFUEL SWEDEN AB
- Current Assignee: ORGANOFUEL SWEDEN AB
- Current Assignee Address: SE Sundsvall
- Agency: Whitmyer IP Group LLC
- International Application: PCT/EP2015/079869 WO 20151215
- International Announcement: WO2016/096905 WO 20160623
- Main IPC: C07D307/34
- IPC: C07D307/34 ; C07C209/28 ; C07D317/58 ; C07C41/18 ; C07C41/26 ; C07C45/38 ; C07C213/02 ; C07C227/08 ; C07C231/02 ; C07D307/52 ; B01J23/44 ; B01J31/02 ; B01J35/00 ; B01J35/04

Abstract:
A mild and efficient synthesis of primary amines and amides from aldehydes or ketones using a heterogeneous metal catalyst and amine donor is disclosed. The initial heterogeneous metal-catalyzed reaction between the carbonyl and the amine donor components is followed by the addition of a suitable acylating agent component in one-pot, thus providing a catalytic one-pot three-component synthesis of amides. Integration of enzyme catalysis allows for eco-friendly one-pot co-catalytic synthesis of amides from aldehyde and ketone substrates, respectively. The process can be applied to asymmetric synthesis or to the co-catalytic one-pot three-component synthesis of capsaicin and its analogues from vanillin or vanillyl alcohol. A co-catalytic reductive amination/dynamic kinetic resolution (dkr) relay sequence for the asymmetric synthesis of optically active amides from ketones is disclosed. Implementation of a catalytic reductive amination/kinetic resolution (kr) relay sequence produces the corresponding optically active amide product and optical active primary amine product with the opposite stereochemistry from the starting ketones.
Public/Granted literature
- US20170362162A1 SYNTHESIS OF AMIDES AND AMINES FROM ALDEHYDES OR KETONES BY HETEROGENEOUS METAL CATALYSIS Public/Granted day:2017-12-21
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