Developing an Asymmetric Transfer Hydrogenation Process
for (S)‑5-Fluoro-3-methylisobenzofuran-1(3H)‑one, a Key Intermediate to Lorlatinib
Version 3 2018-02-09, 23:13
Version 2 2017-10-17, 17:56
Version 1 2017-07-18, 21:03
Posted on 2018-02-09 - 23:13
Synthesis
of (S)-5-fluoro-3-methylisobenzofuran-1(3H)-one (6), a key intermediate to lorlatinib,
is described. A few synthetic methodologies, that is, boron reduction,
enzymatic reduction, asymmetric hydrogenation, and asymmetric transfer
hydrogenation, were evaluated for the chiral reduction of the substituted
acetophenone intermediate (8). A manufacturing process,
on the basis of the asymmetric transfer hydrogenation, was developed.
This process was successfully scaled up to prepare 400 kg of 6.
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Duan, Shengquan; Li, Bryan; Dugger, Robert W.; Conway, Brian; Kumar, Rajesh; Martinez, Carlos; et al. (2017). Developing an Asymmetric Transfer Hydrogenation Process
for (S)‑5-Fluoro-3-methylisobenzofuran-1(3H)‑one, a Key Intermediate to Lorlatinib. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.7b00187
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AUTHORS (10)
SD
Shengquan Duan
BL
Bryan Li
RD
Robert W. Dugger
BC
Brian Conway
RK
Rajesh Kumar
CM
Carlos Martinez
TM
Teresa Makowski
RP
Robert Pearson
MO
Mark Olivier
RC
Roberto Colon-Cruz