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

HRID 1499925노트

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HRID 1499925 반응식
[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

참가 물질

4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-460181c75ee148f39c4ce75b4fde6bec
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199982B2

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