Water → (4-Methyloxan-4-yl)methanamine

HRID 1623318ノート

反応式

HRID 1623318 の反応式
[CH3:1][C:2]1([C:8]#[N:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.O.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH2:8][NH2:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 235743174-Methyltetrahydro-2H-pyran-4-carbonitrileHCID 68718528lithium aluminium hydride THF

生成物 1

HCID 54165201(4-Methyloxan-4-yl)methanamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-methyltetrahydro-2H-pyran-4-carbonitrile (1.8 g, 14.38 mmol) in THF (30 mL) was added carefully 1M LAH/THF (21.57 mL, 21.57 mmol) at 0° C. The reaction mixture was stirred for 15 min at 0° C., allowed to warm to ambient temperature and stirred for ˜3 hours at ambient temperature. To the reaction mixture was carefully added water (0.9 mL), 1N aqueous NaOH (2.7 mL) and water (0.9 mL) [Caution: gas development!]. The mixture was vigorously stirred for 30 min. The precipitate was filtered off and rinsed with THF. The solution was concentrated in vacuo providing crude (4-methyltetrahydro-2H-pyran-4-yl)methanamine as a yellowish solid, which was directly used in the next step without further purification. Yield: 1.54 g. LCMS (m/z): 130.1 [M+H]+; Retention time=0.21 min.

後処理

  1. temperatureto warm to ambient temperature
  2. stirringstirred for ˜3 hours at ambient temperature
  3. stirringThe mixture was vigorously stirred for 30 min
  4. filtrationThe precipitate was filtered off
  5. washrinsed with THF
  6. concentrationThe solution was concentrated in vacuo

出典と根拠

ORDレコード
ord-c94f57826ce0400696bbbb595984c857
出典データセット
uspto-grants-2014_07
特許番号
US08778951B2

反応ノート

読み込み中…