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Stereoselective Synthesis of (S)-3-(Methylamino)-3-((R)-pyrroli
d
in-3-yl)propanenitrile
详细信息
查看全文
作者:
Manjin
d
er S. Lall
;
Garrett Hoge
;
Tuan P. Tran
;
William Kissel
;
Sean T. Murphy
;
Clarke Taylor
;
Kim Hutchings
;
Brian Samas
;
E
d
mun
d
L. Ellsworth
;
Timothy Curran
;
H.
D
.
Hollis
Showalter
刊名:The Journal of Organic Chemistry
出版年:2012
出版时间:May 18, 2012
年:2012
卷:77
期:10
页码:4732-4739
全文大小:415K
年卷期:v.77,no.10(May 18, 2012)
ISSN:1520-6904
文摘
(
S
)-3-(Methylamino)-3-((
R
)-pyrroli
d
in-3-yl)propanenitrile (
1
) is a key interme
d
iate in the preparation of PF-00951966,
d(0);" class="ref">(1) a fluoroquinolone antibiotic for use against key pathogens causing community-acquire
d
respiratory tract infections inclu
d
ing multi
d
rug resistant (MDR) organisms. The current work
d
escribes the
d
evelopment of a highly efficient an
d
stereoselective synthesis of
1
in 10 steps with an overall yiel
d
of 24% from rea
d
ily available benzyloxyacetyl chlori
d
e. Two key transformations in the synthetic sequence involve (a) catalytic asymmetric hy
d
rogenation with chiral DM-SEGPHOS-Ru(II) complex to affor
d
尾-hy
d
roxy ami
d
e
11b
in goo
d
yiel
d
(73%) an
d
high stereoselectivity (
d
e 98%, ee >99%) after recrystallization an
d
(b) S
N
2 substitution reaction with methylamine to provi
d
e
d
iamine
14
with inversion of configuration at the 1鈥?position in high yiel
d
(80%), after efficient purification using a simple aci
d
/base extraction protocol.
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