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

HRID 561601
ノート
印刷プレビュー

反応式

HRID 561601 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:19]1[C:27]2[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[CH2:13][C:14](OCC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:19]1[C:27]2[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[CH2:13][CH2:14][OH:15]
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 58392306Ethyl 3-[2-chloro-4-(trifluoromethyl)phenyl]-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

生成物 1

HCID 583922483-[2-Chloro-4-(trifluoromethyl)phenyl]-3-{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 1.30 g (2.85 mmol) of the compound from Example 99A in 20 ml of THF was added dropwise to 10 ml (9.98 mmol) of a 1N lithium aluminum hydride solution in THF under argon in 80 ml of THF at RT. 1N hydrochloric acid was then added, the mixture was extracted with dichloromethane, 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 0.73 g (61% of theory) of the title compound.

後処理

  1. extractionthe mixture was extracted with dichloromethane
  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-3a3bc7ea155a48c69eed851731d066b7
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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