Methyl iodide → HCID 59201629, compound

HRID 451870Notes

Reaction equation

HRID 451870 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([CH3:22])([CH3:21])[CH2:6][C@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH3:23]I>CN(C=O)C>[CH3:23][O:3][CH2:4][C:5]([CH3:22])([CH3:21])[CH2:6][C@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22882486HCID 22882486, compound

Product 1

HCID 59201629HCID 59201629, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (2.76 g, 69 mmol) in DMF (100 mL) was added dropwise a solution of (S)-tert-butyl 4-(3-hydroxy-2,2-dimethylpropyl)-2,2-dimethyloxazolidine-3-carboxylate (6.6 g, 23 mmol) in DMF (150 mL). After the reaction mixture was stirring for 2 h, MeI (6.53 g, 46 mmol) was added dropwise. The mixture was quenched with NH4Cl (100 mL) and extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. (S)-tert-butyl 4-(3-methoxy-2,2-dimethylpropyl)-2,2-dimethyloxazolidine-3-carboxylate (6.4 g, 93%) was obtained as an oil that was used in the next step without further purification.

Workup

  1. customThe mixture was quenched with NH4Cl (100 mL)
  2. extractionextracted with EtOAc (100 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d1b227e8be34c5d9400c95d88d4f5e7
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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