Ammonium Chloride → 8-Fluoro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971017ノート

反応式

HRID 1971017 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:24]#[N:25])=[CH:12][N:13]=[C:14]([NH:15][C@@H:16]4[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][C@H:17]4[CH3:23])[C:5]=3[C:4]=2[CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.[Cl-].[Na+].O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:24]#[N:25])=[CH:12][N:13]=[C:14]([NH:15][C@@H:16]4[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18][C@H:17]4[CH3:23])[C:5]=3[C:4]=2[CH:3]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 686689758-Fluoro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

生成物 1

HCID 686691058-Fluoro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of 8-fluoro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (7.23 g, 21.5 mmol) in MeOH (100 mL) was added sodium borohydride (1.63 g, 43.0 mmol) at 0° C. The reaction mixture was left to stir at room temperature for 1 h, treated with aqueous ammonium chloride and brine, and extracted with EtOAc. The combined organics were dried (sodium sulfate), and concentrated. The diastereomers were separated by flash chromatography to afford the title compound. LRMS (APCI) calc'd for (C19H19FN4O) [M+H]+, 339.2. found 339.1.

後処理

  1. waitThe reaction mixture was left
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe diastereomers were separated by flash chromatography

出典と根拠

ORDレコード
ord-531337469df14da28b7a64704185f952
出典データセット
uspto-grants-2013_04
特許番号
US08431569B2

反応ノート

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