Aluminium lithium hydride → benzyl 3-fluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

HRID 1179475노트

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HRID 1179475 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26](OC)=[O:27])=[C:20]([F:30])[CH:19]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[F:30][C:20]1[CH:19]=[C:18]([NH:17][C:15](=[O:16])[O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:23]=[CH:22][C:21]=1/[CH:24]=[CH:25]/[CH2:26][OH:27]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 58978082methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)acrylate

생성물 1

HCID 11392443benzyl 3-fluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

A THF solution of LiAlH4 (10.2 mL of a 1.0 M solution, 10.2 mmol) was added to a cooled (−78° C.) solution of methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)acrylate (3.35 g, 10.2 mmol) in TBF (50 mL). The solution was allowed to warm slowly to −20° C. and maintained at that temperature for 2 hours. The reaction mixture was quenched by slow addition of saturated NH4Cl and then treated with 30 mL of dilute citric acid. The resulting solution was stirred for 15 minutes and then extracted with three portions of ethyl acetate. Combined organic phases were washed with H2O, brine and dried (MgSO4), filtered and concentrated to give a red oil. The crude product was purified by column chromatography (25-50% ethyl acetate-hexane) to provide the title compound as a yellow solid.

후처리

  1. temperaturemaintained at that temperature for 2 hours
  2. customThe reaction mixture was quenched by slow addition of saturated NH4Cl
  3. additiontreated with 30 mL of dilute citric acid
  4. extractionextracted with three portions of ethyl acetate
  5. washCombined organic phases were washed with H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a red oil
  10. customThe crude product was purified by column chromatography (25-50% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-012b3977dd1a4535be0a560760f95e7a
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279494B2

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