Methyl iodide → HCID 70673628, compound

HRID 1910498Notes

Reaction equation

HRID 1910498 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:31])[O:15][CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:32][CH3:33]>CCOC(C)=O>[I-:32].[CH2:1]([N+:8]1([CH3:33])[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]([O:15][CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[O:31])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 70926013HCID 70926013, compound

Product 1

HCID 70673628HCID 70673628, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-bis(3-fluorophenyl)methyl 1-benzylpyrrolidin-3-ylcarbamate (300 mg, 0.71 mmol) in EtOAc (9 ml), iodomethane (44.2 μl, 0.71 mmol) was added, and the reaction was stirred at room temperature overnight. The solvent was then removed under vacuum, and the residue was triturated with diethyl ether. The product was purified by flash chromatography (DCM/MeOH=99/1) and then by preparative HPLC to give (3R)-1-benzyl-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-methylpyrrolidinium iodide (25 mg).

Workup

  1. customThe solvent was then removed under vacuum
  2. customthe residue was triturated with diethyl ether
  3. customThe product was purified by flash chromatography (DCM/MeOH=99/1)

Sources & evidence

ORD record
ord-ddd2674a4bb94838a342d3b87f554778
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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