Methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate → Methyl (2S)-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 2264831Notes

Reaction equation

HRID 2264831 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[CH:12][N:11]=1)[C:3]([O:5][CH3:6])=[O:4]>C(#N)C.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]2[CH2:8][CH2:7][C@@H:2]([C:3]([O:5][CH3:6])=[O:4])[N:1]=2)=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 59596690Methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate

Product 1

HCID 59596699Methyl (2S)-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-3,4-dihydro-2H-pyrrole-2-carboxylateYield 100.4%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate (D84, 300 mg, 0.91 mmol) in acetonitrile was added silver triflate (24 mg, 0.091 mmol) and the mixture was stirred for 60 hours at room temperature. The solvent was evaporated and the residue diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated affording the title compound as a yellow solid (300 mg, quantitative). Rt (HPLC): 3.58 min; MS: (ES/+) m/z: 329 [MH]+ C18H17FN2O3 requires 328.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-15b89085943d44daa82387a4214e9ab0
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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