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

HRID 246124ノート

反応式

HRID 246124 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒2 回HCID 6342Acetonitrile溶媒

実験手順

((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.

後処理

  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)

出典と根拠

ORDレコード
ord-8412e720ae5945539cdf385cac254d75
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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