Methyl iodide → tert-butyl [(2R)-2-methoxypropyl]carbamate

HRID 1948388Notes

Reaction equation

HRID 1948388 reaction equation
[OH:1][C@H:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[H-].[Na+].[CH3:15]I>C1COCC1>[CH3:15][O:1][C@H:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12094522N-Boc-(R)-1-amino-2-propanol

Product 1

HCID 86641515tert-butyl [(2R)-2-methoxypropyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [(2R)-2-hydroxypropyl]carbamate (0.4 g, 2.28 mmol) in THF (5 mL), sodium hydride (0.06 g, 2.51 mmol) was added at 0° C. The resulting solution was stirred for 30 minutes at that temperature and then methyl iodide (0.14 mL, 2.28 mmol) was added. The reaction was warmed to room temperature slowly and allowed to stir for an additional two hours. The reaction was quenched by adding water and extracted with ethyl acetate. The extract was washed with sodium bicarbonate solution, water and brine. It was dried over magnesium sulfate and concentrated. The desired product was obtained as clear oil (0.31 g) and it did not need any further purification.

Workup

  1. stirringto stir for an additional two hours
  2. customThe reaction was quenched
  3. additionby adding water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with sodium bicarbonate solution, water and brine
  6. dry with materialIt was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-970a343624754a1084a645a79af878a1
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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