ChemicalBook CAS DataBase List 1-(1,1-Dimethylethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate

1-(1,1-Dimethylethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate synthesis

10synthesis methods

Product Name:1-(1,1-Dimethylethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate
CAS Number:203866-14-2
Molecular formula:C10H16FNO4
Molecular Weight:233.24

(2R,4S)-N-BOC-4-fluoro-D-proline is a pharmaceutical intermediate that can be used to prepare NS5A inhibitors. It can be obtained from N-Boc-trans-4-hydroxy-L-proline methyl ester as raw material, firstly fluorinated to obtain N-Boc-trans-4-fluoro-L-proline methyl ester, then hydrolyzed.

203866-18-6 Synthesis

BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER

203866-18-6
119 suppliers
$14.00/250mg

1-(1,1-Dimethylethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate

203866-14-2
210 suppliers
$23.30/1G

Yield:-

Steps:

G

The fluorination of the above cis-hydroxy provides the trans-4-fluoro derivative which on saponification gives the corresponding acid. The amine is prepared from 4-R-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester and 5-methyl-pyridin-2-ylamine under HATU condition to give proline amide derivative which on treatment with 4 M HCl in dioxane provides the desired amine.

References:

US2009/62537,2009,A1 Location in patent:Page/Page column 10