Water → 3-Chloro-4-[4-(3',6'-dihydro[2,4'-bipyridin]-1'(2'H)-yl)butyl]-1,4-benzoxazepin-5(4H)-one

HRID 1250309Notes

Reaction equation

HRID 1250309 reaction equation
[Cl-].[Cl:2][C:3]1[N:9]([CH2:10][CH2:11][CH2:12][CH:13]=[N+:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:16][CH2:15]2)[C:8](=[O:26])[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=2[O:5][CH:4]=1.[BH4-].[Na+].O>C(O)C>[Cl:2][C:3]1[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:16][CH2:15]2)[C:8](=[O:26])[C:7]2[CH:27]=[CH:28][CH:29]=[CH:30][C:6]=2[O:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 69690191HCID 69690191, compound

Product 1

HCID 98016403-Chloro-4-[4-(3',6'-dihydro[2,4'-bipyridin]-1'(2'H)-yl)butyl]-1,4-benzoxazepin-5(4H)-oneYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

800 mg of the compound of Example 23 was dissolved in 20 ml of ethanol, 140 mg (2 equivalents) of sodium borohydride was added under ice cooling, then the result was agitated at room temperature for 10 minutes. Water was added and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated saline, then was dried with anhydrous magnesium sulfate. The solvent was distilled off and the resultant crude product was refined with silica gel column chromatography (methylene chloride:methanol=30:1), to obtain the above-referenced compound in an amount of 600 mg (yield of 81%).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customto obtain the above-referenced compound in an amount of 600 mg (yield of 81%)

Sources & evidence

ORD record
ord-20b4eda5da8841eb99f820f76a8f651b
Source dataset
uspto-grants-2002_01
Patent number
US06337397B1

Reaction notes

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