Water → 3-(4-Chlorophenyl)-3-{6-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561527ノート

反応式

HRID 561527 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])[C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(#N)C.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:25][S:26][CH3:27])[C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 6342AcetonitrileHCID 21226445Aluminium lithium hydrideHCID 58392255Ethyl 3-(4-chlorophenyl)-3-{6-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

生成物 1

HCID 583923413-(4-Chlorophenyl)-3-{6-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
60 °C

実験手順

A solution of 2.33 g (5.7 mmol) of the compound from Example 47A in 18 ml of tetrahydrofuran was added dropwise to 20.1 ml (60.1 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran and 20 ml of tetrahydrofuran at RT. The mixture was stirred at 60° C. for 1 h, acetonitrile was added, and water was added to the solution while cooling in ice. The solid was filtered off with suction from the suspension, the filtrate was concentrated, and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 1.72 g (82% of theory) of the title compound were obtained.

後処理

  1. temperaturewhile cooling in ice
  2. filtrationThe solid was filtered off with suction from the suspension
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

出典と根拠

ORDレコード
ord-1994f88aa1fd4d3287a15a240387ad6f
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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