Aluminium lithium hydride → (R)-3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propan-1-ol

HRID 657762노트

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HRID 657762 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]([C@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:32])[C@@H:15]([C:24]1[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1)[CH2:16][C:17](OC(C)(C)C)=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]([C@H:31]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH3:32])[C@@H:15]([C:24]1[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1)[CH2:16][CH2:17][OH:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 66871888(R)-tert-butyl 3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propanoate

생성물 1

HCID 58103596(R)-3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
75 °C

실험 절차

To a solution of LiAlH4 (1.24 g, 32.79 mmol) in THF (80 mL) at 0° C., was added dropwise a solution of (R)-tert-butyl 3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propanoate (4.7 g, 10.93 mmol) in THF and was heated to 75° C. After 4 h, the reaction mixture was quenched with EtOAc and filtered. The filtrate was washed with excess EtOAc and dried under high vacuum to afford a residue. Purification of the residue by column chromatography (neutral Al2O3, Et2O/Pet ether 15:85) afforded the title compound.

후처리

  1. customthe reaction mixture was quenched with EtOAc
  2. filtrationfiltered
  3. washThe filtrate was washed with excess EtOAc
  4. customdried under high vacuum
  5. customto afford a residue
  6. customPurification of the residue by column chromatography (neutral Al2O3, Et2O/Pet ether 15:85)

출처 및 근거

ORD 기록
ord-ede8050723c64f3a8e66e18f03a67612
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076345B2

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