Sodium borohydride → 6-Chloro-3-ethoxy-4-(1-hydroxyethyl)-2-(3-methoxyazetidin-1-yl)benzonitrile

HRID 1499925ノート

反応式

HRID 1499925 の反応式
[C:1]([C:4]1[CH:11]=[C:10]([Cl:12])[C:7]([C:8]#[N:9])=[C:6]([N:13]2[CH2:16][CH:15]([O:17][CH3:18])[CH2:14]2)[C:5]=1[O:19][CH2:20][CH3:21])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:12][C:10]1[C:7]([C:8]#[N:9])=[C:6]([N:13]2[CH2:16][CH:15]([O:17][CH3:18])[CH2:14]2)[C:5]([O:19][CH2:20][CH3:21])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:11]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866778424-Acetyl-6-chloro-3-ethoxy-2-(3-methoxyazetidin-1-yl)benzonitrile

生成物 1

HCID 866778436-Chloro-3-ethoxy-4-(1-hydroxyethyl)-2-(3-methoxyazetidin-1-yl)benzonitrile収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

4-Acetyl-6-chloro-3-ethoxy-2-(3-methoxyazetidin-1-yl)benzonitrile (30 mg, 0.1 mmol was dissolved in methanol (5 mL) cooled to 0° C. and sodium tetrahydroborate (5.5 mg, 0.14 mmol) was added. Reaction was stirred for 1 h at 0° C. The reaction was partitioned between EtOAc and water. The combined organic layer was washed with water and saturated NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give crude 6-chloro-3-ethoxy-4-(1-hydroxyethyl)-2-(3-methoxyazetidin-1-yl)benzonitrile (0.030 g, 100%). LCMS calculated for C15H20ClN2O3(M+H)+: m/z=311.1; found: 311.1.

後処理

  1. customReaction
  2. customThe reaction was partitioned between EtOAc and water
  3. washThe combined organic layer was washed with water and saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-460181c75ee148f39c4ce75b4fde6bec
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

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