HCID 59596677, compound → methyl (2S)-5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 2264824Notes

Reaction equation

HRID 2264824 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]>C(#N)C.[Cl-].[Na+].O.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]2[CH2:8][CH2:7][C@@H:2]([C:3]([O:5][CH3:6])=[O:4])[N:1]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 1

HCID 59596677HCID 59596677, compound

Product 1

HCID 59596717methyl (2S)-5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylateYield 103%

Reagents, catalysts & solvents 3

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methyl (2S)-2-amino-5-(4-bromophenyl)-4-pentynoate (D75, 849 mg, 3.009 mmol) and silver-(I)-triflate in acetonitrile (30 ml) was stirred overnight at room temperature. Then brine was added and the product was extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered and evaporated to afford the title compound (874 mg, 96%). UPLC: Rt 0.70 min; MS: (ES/+) m/z: 282, 284 [MH+], C12H12BrNO2 requires 282.

Workup

  1. extractionthe product was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-470589744cef4057b05d7ec205785450
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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