(2S,4R)-1-(tert-Butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid → (2S,4R)-N-(4-(4-fluoro-3-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide

HRID 1630069Notes

Reaction equation

HRID 1630069 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[CH3:16].C(OC([N:24]1[CH2:28][C@H:27]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH2:26][C@H:25]1[C:37](O)=[O:38])=O)(C)(C)C>>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:37]([C@@H:25]3[CH2:26][C@@H:27]([CH2:29][C:30]4[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)[CH2:28][NH:24]3)=[O:38])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[CH3:16]

Participants

3

Reactant 2

HCID 2761972(2S,4R)-1-(tert-Butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acidHCID 67009392HCID 67009392, compound

Product 1

HCID 67009472(2S,4R)-N-(4-(4-fluoro-3-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamideYield 73%

Procedure

Proceeding as in Reference 6, but substituting 4-(4-fluoro-3-methylphenoxy)aniline and (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid, gave (2S,4R)—N-(4-(4-fluoro-3-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide (282 mg, 73%).

Sources & evidence

ORD record
ord-8881d5ef1a414e7398f5a80be793d299
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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