Methyl iodide → HCID 86711838, compound

HRID 623753Notes

Reaction equation

HRID 623753 reaction equation
[H-].[Na+].[CH3:3][C:4]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)([CH3:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:21]I>CN(C=O)C.O>[CH3:21][N:6]([CH2:5][C:4]([CH3:3])([N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 63789558HCID 63789558, compound

Product 1

HCID 86711838HCID 86711838, compoundYield 119.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% NaH in mineral oil (238 mg, 5.96 mmol) in dry DMF (5 mL) was added dropwise a solution of tert-butyl 2-methyl-2-morpholinopropylcarbamate (770 mg, 2.98 mmol) in dry DMF (5 mL). After 30 min MeI (0.928 mL, 14.9 mmol) was added dropwise. The mixture was stirred at room temperature for 5 d, poured in H2O and extracted with Et2O (30 mL). The organic layer was dried (Na2SO4) and concentrated to yield the desired crude product (970 mg,) as a light yellow oil.

Workup

  1. extractionextracted with Et2O (30 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2afc74a8aafd420fae0c9aa97665e275
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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