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

HRID 246124Notes

Reaction equation

HRID 246124 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].I[CH3:14]>C(#N)C.[Ag]=O>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([O:11][CH3:14])[CH3:10])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 6328Methyl iodide2×HCID 11789722N-Boc-(S)-1-amino-2-propanol

Product 1

HCID 86643351tert-butyl N-[(2S)-2-methoxypropyl]carbamateYield 32%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

((S)-2-Hydroxy-propyl)-carbamic acid tert-butyl ester (0.25 g, 1.43 mmol) was dissolved in acetonitrile (14 ml) and iodomethane (1.78 ml, 28.5 mmol), and then silver oxide (0.53 g, 2.28 mmol; prepared as in Org. Syn. Coll. Vol. VII, p. 386) were added. The reaction flask was covered to protect from light and the reaction was heated at reflux for 24 h. Additional iodomethane (1.8 ml) and silver oxide (0.26 g) were added and heating was continued until the reaction was judged to be complete by standard reverse phase LC/MS. The reaction mixture was filtered through diatomaceous earth, rinsing with ethyl acetate. After evaporation the residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give 85 mg (32%) of ((S)-2-methoxy-propyl)-carbamic acid tert-butyl ester. (M+Na)+=212.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 24 h
  3. temperatureheating
  4. filtrationThe reaction mixture was filtered through diatomaceous earth
  5. washrinsing with ethyl acetate
  6. customAfter evaporation the residue
  7. customwas purified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8412e720ae5945539cdf385cac254d75
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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