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(3R)-3-hydroxy-3-phenylpropanenitrile → (1R)-3-amino-1-phenylpropan-1-ol

HRID 1760079
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HRID 1760079 반응식
[C:1]1([C@H:7]([OH:11])[CH2:8][C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([C@H:7]([OH:11])[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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참가 물질

3

반응물 1

HCID 10130035(3R)-3-hydroxy-3-phenylpropanenitrile

생성물 1

HCID 11182697(1R)-3-amino-1-phenylpropan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a THF solution of (R)-3-phenyl-3-hydroxypropanenitrile was slowly added borane dimethyl sulfide complex at room temperature. Methyl sulfide was then distilled from the reaction vessel and the resulting THF solution refluxed for 2.5 h. After cooling to room temperature methanolic HCl was added to the reaction mixture. Methanol and methyl borate were removed by distillation and the reaction mixture neutralized with sodium hydroxide (5N). Extraction of the mixture with dichloromethane followed by concentration provided the crystalline (R)-3-phenyl-3-hydroxypropylamine.

후처리

  1. customat room temperature
  2. distillationMethyl sulfide was then distilled from the reaction vessel
  3. temperaturethe resulting THF solution refluxed for 2.5 h
  4. additionwas added to the reaction mixture
  5. customMethanol and methyl borate were removed by distillation
  6. extractionExtraction of the mixture with dichloromethane
  7. concentrationfollowed by concentration

출처 및 근거

ORD 기록
ord-a0ada6ef4b0b43e88a2d67c69f08646f
출처 데이터셋
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06838581B2

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