Hydrochloric Acid → 1-[4-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-2,3-difluoro-5-hydroxymethyl-phenyl]-ethanone

HRID 245357ノート

反応式

HRID 245357 の反応式
C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C:8]1[C:9]([N:19]2[CH2:24][C@H:23]([CH3:25])[O:22][C@H:21]([CH3:26])[CH2:20]2)=[C:10]([F:18])[C:11]([F:17])=[C:12]([C:14](=[O:16])[CH3:15])[CH:13]=1)(C)(C)C.Cl.O>O1CCOCC1>[CH3:25][C@H:23]1[O:22][C@@H:21]([CH3:26])[CH2:20][N:19]([C:9]2[C:8]([CH2:7][OH:6])=[CH:13][C:12]([C:14](=[O:16])[CH3:15])=[C:11]([F:17])[C:10]=2[F:18])[CH2:24]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178466840HCID 178466840、化合物2 回

生成物 1

HCID 866580491-[4-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-2,3-difluoro-5-hydroxymethyl-phenyl]-ethanone

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-2,3-difluoro-phenyl]-ethanone (Intermediate 9, 7.2 g, 28 mmol) and 4N HCl in dry dioxane (75 mL) was stirred at room temperature for 12 hours. The reaction mixture was treated with cold water (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases combined were dried (Na2SO4) and concentrated. The residue was purified over a silica gel flash column using a gradient of ethyl acetate in pet. ether to give the title compound as yellow solid.

後処理

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic phases combined were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified over a silica gel flash column

出典と根拠

ORDレコード
ord-c2f40ccf6e3449c5bf7ac489e8c90927
出典データセット
uspto-grants-2014_02
特許番号
US08658641B2

反応ノート

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