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Hydrochloric Acid → 3-(4-Chloro-2-methylphenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561600
ノート
印刷プレビュー

反応式

HRID 561600 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:25][S:26][CH3:27])[CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[C:4]([CH3:28])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:25][S:26][CH3:27])[CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[C:4]([CH3:28])[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392476Ethyl 3-(4-chloro-2-methylphenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

生成物 1

HCID 583921093-(4-Chloro-2-methylphenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒
3 回

実験手順

A solution of 690 mg (1.64 mmol) of the compound from Example 98A in 10 ml of THF was added dropwise to 5.8 ml (5.75 mmol) of a 1N lithium aluminum hydride solution in THF under argon in 20 ml of THF at RT. 1N hydrochloric acid was then added, the mixture was extracted with ethyl acetate, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 0.60 g (97% of theory) of the title compound.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

出典と根拠

ORDレコード
ord-d93bba2fa21345d3aed9d697a075e2d8
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063234B2

反応ノート

読み込み中…

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