Methyl iodide → 3,5-Dichlorobenzyl 2-(2-((tert-butoxycarbonyl)(methyl)amino)ethyl)morpholine-4-carboxylate

HRID 1480384Notes

Reaction equation

HRID 1480384 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[O:18])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:32]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]([CH3:32])[CH2:9][CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[O:18])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 867226343,5-Dichlorobenzyl 2-(2-((tert-butoxycarbonyl)amino)ethyl)morpholine-4-carboxylate

Product 1

HCID 867226363,5-Dichlorobenzyl 2-(2-((tert-butoxycarbonyl)(methyl)amino)ethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture comprising of 3,5-dichlorobenzyl 2-(2-((tert-butoxycarbonyl)amino)ethyl)morpholine-4-carboxylate (Example 11, step 1) (1 g, 2.308 mmol) and sodium hydride (60% in oil) (0.111 g, 2.77 mmol) in DMF (20 mL) was stirred at 0° C. for 15 minutes. Iodomethane (0.216 mL, 3.46 mmol) was added and the mixture was left to stir at room temperature for 16 hours. The reaction was quenched with water (10 ml) to form a suspension. The suspension was diluted with H2O (100 ml) and extracted with EtOAc (200 ml). The organic portion was separated and washed with H2O (100 ml), dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound;

Workup

  1. waitthe mixture was left
  2. customThe reaction was quenched with water (10 ml)
  3. customto form a suspension
  4. extractionextracted with EtOAc (200 ml)
  5. customThe organic portion was separated
  6. washwashed with H2O (100 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c7b696664ae4076822d71299b509d71
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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