4-tert-Butylphenyl glycidyl ether, (+)- → (S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 237730ノート

反応式

HRID 237730 の反応式
[N:1]#[C:2][NH2:3].[Na].[C:5]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@@H:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>CO>[C:5]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@H:15]2[O:16][C:2]([NH2:3])=[N:1][CH2:17]2)=[CH:11][CH:10]=1)([CH3:6])([CH3:7])[CH3:8]

参加物

4

反応物 2

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-HCID 57375518Cyanamidnatrium

生成物 1

HCID 67060987(S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine収率 41%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a vigorously stirred solution of sodium hydrogen cyanamide (2.92 g, 44.5 mmol) in methanol (40 mL) was added dropwise (S)-2-(4-tert-butylphenoxymethyl)-oxirane (9.18 g, 44.5 mmol). The reaction mixture was stirred at room temperature overnight after which the reaction mixture was concentrated to remove methanol. Anhydrous diethyl ether (150 mL) was added. The resulting white precipitate was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 4.53 g (41%) of (S)-5-(4-tert-butyl-phenoxymethyl)-(4,5-dihydro-oxazol-2-yl)amine.

後処理

  1. concentrationwas concentrated
  2. customto remove methanol
  3. additionAnhydrous diethyl ether (150 mL) was added
  4. filtrationThe resulting white precipitate was filtered through celite
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

出典と根拠

ORDレコード
ord-626b2a8eccaf447a9d00c52e8afc40d5
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

反応ノート

読み込み中…