Methyl iodide → Benzyl [(1R)-2-methoxy-1-methylethyl]carbamate

HRID 1948387Notes

Reaction equation

HRID 1948387 reaction equation
[OH:1][CH2:2][C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].[CH3:16]I>C(#N)C.[Ag]=O>[CH3:16][O:1][CH2:2][C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 6951254Benzyl ((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 86643350Benzyl [(1R)-2-methoxy-1-methylethyl]carbamateYield 71.5%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of benzyl [(1R)-2-hydroxy-1-methylethyl]carbamate (0.5 g, 2.38 mmol) in acetonitrile (20 mL), silver oxide (3.8 g, 13.09 mmol) is added followed by the addition of methyl iodide (1.94 mL, 23.8 mmol). The resultant mixture was stirred overnight at room temperature. The insoluble salt was filtered off and the filtrate was concentrated. The residue was flashed using silica and Ethyl acetate/hexanes system as eluent to give the desired product as clear oil (0.38 g).

Workup

  1. filtrationThe insoluble salt was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-623a13dc66014028b2ce2f1c8414dec1
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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