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

HRID 1179475ノート

反応式

HRID 1179475 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-012b3977dd1a4535be0a560760f95e7a
出典データセット
uspto-grants-2007_10
特許番号
US07279494B2

反応ノート

読み込み中…