Acetic Acid → (2Rs,5rs)-4-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-n-butyramidine

HRID 1357160Notes

Reaction equation

HRID 1357160 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]([CH2:23][CH2:24][CH2:25][C:26]([NH:28]O)=[NH:27])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)(=O)C>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:14])=[O:15])[CH:11]([CH2:23][CH2:24][CH2:25][C:26]([NH2:28])=[NH:27])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178427370HCID 178427370, compound

Product 1

HCID 22250424(2Rs,5rs)-4-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-n-butyramidineYield 76.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2RS,5RS)-4-[5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-N-hydroxy-butyramidine (1.1 g, 2.62 mmol) was dissolved in EtOH (50 ml) and acetic acid (5 ml) and hydrogenated on Ra—Ni at room temperature for 2 h. The catalyst was filtered off, the filtrate evaporated and the crude product crystallized from saturated NaHCO3 solution to give (2RS,5RS)-4-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-N-butyramidine (0.81 g, 76%) as a light brown solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customthe crude product crystallized from saturated NaHCO3 solution

Sources & evidence

ORD record
ord-a7147016ce574350872aa95bfe2435b5
Source dataset
uspto-grants-2003_07
Patent number
US06589978B2

Reaction notes

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