Method for producing endo-9-azabicyclo[3.3.1]nonan-3-ol derivative

Patent metadata

Field	Value
Publication number	US-9896451-B2
Application number	US-201414913736-A
Country	US
Kind code	B2
Filing date	Aug 14, 2014
Priority date	Sep 6, 2013
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

A 9-azabicyclo[3.3.1]nonan-3-one derivative is reacted with a hydrogen in the presence of a catalyst composed of a ruthenium complex to obtain, at a low cost, an endo-9-azabicyclo[3.3.1]nonan-3-ol derivative useful as a production intermediate for agrochemical agents or medicines.

First claim

The invention claimed is:

1. A method for producing a compound represented by formula (II), comprising reacting a compound represented by formula (I) with a hydrogen in a presence of a catalyst consisting of a ruthenium complex:

in the formulae (I) and (II), R represents a benzyl group, and
the ruthenium complex is selected from the group consisting of a RuCl 2 (PPh 3 ) 2 (ethylenediamine), a RuCl 2 (2,2′-bis-(diphenylphosphino)-1,1′-biphenyl)(ethylenediamine), a RuCl 2 (PPh 3 ) 2 (N,N-dimethylethylenediamine), a trans-RuCl 2 (PPh3) 2 (α-picolylamine), a cis-RuCl 2 (PPh 3 ) 2 (α-picolylamine), a rucy catalyst represented by a formula (c):

a RuCl2 [(S)-2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl] [(2R,3R,4R,5R)-3,4-O-isopropylidenehexane-2,5-diamine], a RuCl 2 [2,2′-bis-(diphenylphosphino)-1,1′-biphenyl] [(2S,3S)-2,3-O-isopropylidenebutane-1,4-diamine], a RuCl 2 [(S)-2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl] [(R)-2-dimethylamino-1-phenylethylamine], a RuCl 2 (Ph 2 PCH 2 CH 2 NH 2 ) 2 , a RuCl 2 (tBu 2 PCH 2 CH 2 NH 2 ) 2 , a RuCl 2 (Ph 2 PCH 2 CH 2 CH 2 NH 2 ) 2 , a RuCl 2 [2,2′-bis-(diphenylphosphino)-1,1′-biphenyl] [α-picolylamine], a RuCl 2 [2,2′-bis-(diphenylphosphino)-1,1′-biphenyl] [2-(pyridin-2-yl)ethylamine], a trans-RuCl 2 [2,2′-bis-(diphenylphosphino)-1,1′-biphenyl] [(5-methylpyrazin-2-yl)methanamine], a RuCl 2 [1,4bis(diphenylphosphino)butane] [pyrimidin-2-yl methanamine], a RuCl 2 (1,4-bis(diphenylphosphino)butane) (benzoxazol-2-yl methanamine), a RuCl 2 (1,4-bis(diphenylphosphino)butane)(thiazol-2-yl methanamine), a trans-RuCl 2 [1,4-bis(diphenylphosphino)butane] [(5-methylpyrazin-2-yl) methanamine], a cis-RuCl 2 [1,4-bis(diphenylphosphino)butane] [(5-methylpyrazin-2-yl) methanamine], and a cis-RuCl 2 [1,4-bis(diphenylphosphino)butane] [(1-methyl-1H-benzimidazol-2-yl)methanamine].

Assignees

• Nippon Soda Co

Inventors

• Akashi Masaya
• Inoue Tsutomu
• Oooka Hirohito

Classifications

• B01J31/1815

  with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine · CPC title

• B01J31/2447

  and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring · CPC title

• B01J31/2409

  with more than one complexing phosphine-P atom · CPC title

• B01J31/1805

  the ligands containing nitrogen · CPC title

• C07D451/14

  containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof · CPC title