(2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate → (2S,4R)-4-fluoro-N-(6-fluoropyridin-3-yl)pyrrolidine-2-carboxamide

HRID 1961388Notes

Reaction equation

HRID 1961388 reaction equation
[F:1][C@H:2]1[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([C:14]([O:16]C)=O)[CH2:3]1.F[C@H]1C[N:22](C(OC(C)(C)C)=O)[C@H:21]([C:31](=O)[NH:32][C:33]2[CH:38]=NC=CN=2)[CH2:20]1.[F:40][C@H]1CN[C@H](C(NC2C=NC=CN=2)=O)C1>>[F:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:14]([NH:22][C:21]2[CH:31]=[N:32][C:33]([F:40])=[CH:38][CH:20]=2)=[O:16])[CH2:3]1

Participants

4

Reactant 3

HCID 11806976(2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylateHCID 59436310(2S,4R)-4-Fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamideHCID 59436441(2S,4R)-tert-Butyl 4-fluoro-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 59436330(2S,4R)-4-fluoro-N-(6-fluoropyridin-3-yl)pyrrolidine-2-carboxamide

Procedure

(2S,4R)-4-Fluoro-N-(6-fluoropyridin-3-yl)pyrrolidine-2-carboxamide 79A was prepared from (2S,4R)-1-tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate as described for 65A and 65B. LC/MS [M+H]+: 228; Ret time (Method C): 0.57 min.

Workup

  1. custom0.57 min.

Sources & evidence

ORD record
ord-5940b0c9bbc74ec7aec1f7baaa9840db
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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