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

HRID 1499925Notes

Reaction equation

HRID 1499925 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-460181c75ee148f39c4ce75b4fde6bec
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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