4-Aminocyclohexanecarboxylic acid → ((1s,4s)-4-Aminocyclohexyl)methanol

HRID 525057

反応式

HRID 525057 の反応式
[CH2:1]1[CH:6]([C:7](O)=[O:8])[CH2:5][CH2:4][CH:3]([NH2:10])[CH2:2]1.B.C1COCC1>C1COCC1>[CH2:1]1[CH:6]([CH2:7][OH:8])[CH2:5][CH2:4][CH:3]([NH2:10])[CH2:2]1

参加物

4

反応物 2

HCID 1715604-Aminocyclohexanecarboxylic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 424390((1s,4s)-4-Aminocyclohexyl)methanol収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (1r,4r)-4-aminocyclohexanecarboxylic acid (860 mg, 6.0 mmol, 1.0 eq) in THF (10 mL) was added dropwise BH3/THF (1.0 mol/L in THF, 30 mL, 5.0 equiv.) at 0° C. The reaction was allowed to warm to room temperature. The reaction was heated at reflux for 48 hours. The reaction was quenched with AcOH and concentrated in vacuo to get crude ((1r,4r)-4-aminocyclohexyl)methanol (600 mg, 78%) which was used to the next step without further purification. MS: m/z 130.1 (M+H)+.

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 48 hours
  3. customThe reaction was quenched with AcOH
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3e7a5d5f5a934d9188e5ee27d474ea8e
出典データセット
uspto-grants-2016_05
特許番号
US09340554B2

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