Methyl iodide → HCID 178502718, compound

HRID 1743794Notes

Reaction equation

HRID 1743794 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=[O:20])[N:16]([O:18][CH3:19])[CH3:17])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:25].OS([O-])(=O)=O.[K+]>CC(N(C)C)=O.O.CCOCC>[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15](=[O:20])[N:16]([O:18][CH3:19])[CH3:17])[CH2:13][CH2:14]1)[CH3:25])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 178502721HCID 178502721, compound

Product 1

HCID 178502718HCID 178502718, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21584184Diethylether waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 95 g (corresponds to 301.26 mmol) of crude trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester in 300 ml of DMA was treated at 0° C. with 19.72 g (451.9 mmol) of NaH (55% in oil) in small portions. The reaction was stirred for 1 h at 0° C., then treated slowly (1.5 h) with 150 ml (2.41 mol) of iodomethane. After the addition of 60 ml of iodomethane (1 h), the reaction started, the addition was stopped and continued after reaction was cooled down again. After warming up to RT over night, the reaction was cooled, neutralized with aqueous 10% KHSO4 and poured into water/Et2O (3×). The organic phase was washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (CH2Cl2/EtOAc 9:1 to 1:1) to yield 99 g (quantitative) of trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester, MS: 315 (MH+).

Workup

  1. additionthe addition
  2. customafter reaction
  3. temperaturewas cooled down again
  4. temperatureAfter warming up to RT over night
  5. temperaturethe reaction was cooled
  6. washThe organic phase was washed with aqueous 10% NaCl
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. custompurified by flash silica gel column (CH2Cl2/EtOAc 9:1 to 1:1)

Sources & evidence

ORD record
ord-f5c9495c4eab4723aa1c456f7fd51e6b
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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