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

HRID 525057

반응식

HRID 525057 반응식
[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

참가 물질

4

반응물 2

HCID 1715604-Aminocyclohexanecarboxylic acidHCID 2723981Borane;tetrahydrofuran

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-3e7a5d5f5a934d9188e5ee27d474ea8e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340554B2

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