Methyl iodide → HCID 178476334, compound

HRID 2118240Notes

Reaction equation

HRID 2118240 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22]I.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:22])[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 178476335HCID 178476335, compound

Product 1

HCID 178476334HCID 178476334, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled and stirred solution of the crude 26.0 g trans-acetic acid 4-(2-tert-butoxycarbonylamino-ethyl)-cyclohexylmethyl ester and 5.77 mL (92.6 mmol, 1.1 eq) of CH3I in 300 mL of DMF was added within 15 min 4.04 g (92.58 mmol, 1.1 eq) of NaH (55% in oil). After stirring at RT over night, additional 1.65 mL (26.5 mmol, 0.3 eq) of CH3I and 1.16 g (26.5 mmol, 0.3 eq) of NaH were added and the reaction mixture was then stirred at RT for another 1 h. It was then partitioned between ether, 1M HCl solution and water. The organic layer was dried over MgSO4, concentrated under reduced pressure and the residue was then chromatographed on silica gel with a 4:1 v/v mixture of n-hexane and EtOAc as the eluent giving 18.7 g (68% over 3 steps) of pure trans-acetic acid 4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexylmethyl ester as colorless viscous oil, MS: 214 [(M-(tert-butoxycarbonyl))H+].

Workup

  1. stirringthe reaction mixture was then stirred at RT for another 1 h
  2. customIt was then partitioned between ether, 1M HCl solution and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was then chromatographed on silica gel with a 4:1 v/v mixture of n-hexane and EtOAc as the eluent

Sources & evidence

ORD record
ord-1dfe8647e402420db9b76fc167820084
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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