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2-Amino-2-phenylpropanoic acid → 2-Amino-2-phenylpropan-1-ol

HRID 1911499
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HRID 1911499 반응식
[NH2:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3](O)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[CH2:3][OH:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 317222-Amino-2-phenylpropanoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 3497332-Amino-2-phenylpropan-1-ol수율 59.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred, cooled suspension of 2-amino-2-phenyl-propionic acid (488 mg) at r.t. in THF (10 ml) under an argon atmosphere was added portionwise LiAlH4 (244 mg). The ice bath was removed and stirring at r.t. was then continued for 20 h. The mixture was cooled in an ice bath, diluted with 5 ml THF and H2O (0.23 ml), 4 N NaOH (0.23 ml) and H2O (0.92 ml) were added successively and carefully. After 30 min stirring at r.t., the mixture was filtered and the cake was washed with THF. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 2-amino-2-phenyl-propan-1-ol (266 mg) as colorless viscous oil. MS (ISP): 152.3 ([M+H]+)

후처리

  1. temperatureTo a stirred, cooled
  2. customThe ice bath was removed
  3. temperatureThe mixture was cooled in an ice bath
  4. additiondiluted with 5 ml THF and H2O (0.23 ml), 4 N NaOH (0.23 ml) and H2O (0.92 ml)
  5. additionwere added successively
  6. stirringAfter 30 min stirring at r.t.
  7. filtrationthe mixture was filtered
  8. washthe cake was washed with THF
  9. concentrationThe filtrate was concentrated
  10. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

출처 및 근거

ORD 기록
ord-8017bd5b09104673b8972ec110dafeee
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08604061B2

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