Methyl iodide → HCID 57345356, compound

HRID 1619538Notes

Reaction equation

HRID 1619538 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]([O:12][CH:13]1[CH2:19][CH:18]2[N:20]([CH3:21])[CH:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:28][CH3:29]>CN(C=O)C>[I-:28].[C:1]([O:5][C:6]([NH:8][CH:9]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:10]([O:12][CH:13]1[CH2:14][CH:15]2[N+:20]([CH3:29])([CH3:21])[CH:18]([CH2:17][CH2:16]2)[CH2:19]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 67607346HCID 67607346, compound

Product 1

HCID 57345356HCID 57345356, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(tert-butoxycarbonyl-amino)-2-phenylacetate (C58) (230 mg, 0.61 mmol) in DMF (15 ml), was added iodomethane (42.1 μl, 0.68 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was triturated with i-Pr2O and then purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain 3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane iodide (88.2 mg: 28% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was triturated with i-Pr2O
  3. custompurified by flash chromatography (DCM/MeOH=95/5 to 9/1)

Sources & evidence

ORD record
ord-9f55f8ea51ac4cfa95a628a1b8f53f9f
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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