1-Fluoro-2-nitrobenzene → (2R,4R)-4-Hydroxy-1-(2-Nitrophenyl) Proline Methyl Ester

HRID 1976222Notes

Reaction equation

HRID 1976222 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>>[CH3:2][O:3][C:4](=[O:11])[C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 12764090Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 12042755(2R,4R)-4-Hydroxy-1-(2-Nitrophenyl) Proline Methyl EsterYield 97.2%

Procedure

The same procedures used in Reference Example 1 were repeated except for using the cis-4-hydroxy-D-proline methyl ester hydrochloride prepared in Reference Example 4 and 1-fluoro-2-nitrobenzene to give the title compound. Yield 97.2%.

Sources & evidence

ORD record
ord-fe8e67588dba4de8b9829f76870ea5f9
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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