N-Boc-cis-4-hydroxy-L-proline methyl ester → (2S,4S)-4-Hydroxy-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

HRID 1961390Notes

Reaction equation

HRID 1961390 reaction equation
[OH: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]1CN(C(OC(C)(C)C)=O)[C@H](C(=O)[NH:32][C:33]2[CH:38]=[N:37][CH:36]=[CH:35][N:34]=2)C1.F[C@H]1CN[C@H](C(NC2C=NC=CN=2)=O)C1>>[OH:1][C@@H:2]1[CH2:6][NH:5][C@H:4]([C:14]([NH:32][C:33]2[CH:38]=[N:37][CH:36]=[CH:35][N:34]=2)=[O:16])[CH2:3]1

Participants

4

Reactant 3

HCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterHCID 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 59436319(2S,4S)-4-Hydroxy-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

Procedure

(2S,4S)-4-Hydroxy-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide 85A was prepared from (2S,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate as described for 65A and 65B. LC/MS [M+H]+: 209; Ret time (Method F): 0.27 min.

Workup

  1. custom0.27 min.

Sources & evidence

ORD record
ord-2d82c4324c044bd5804463ac10c91e19
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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