Potassium bisulfate → 1-[(E)-3-(3-chloro-phenyl)-acryloyl]-4-(2-hydroxy-ethyl)-[1,4]diazepan-5-one

HRID 1867404Notes

Reaction equation

HRID 1867404 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[C:12](=[O:13])[CH2:11][CH2:10][N:9]([C:14](=[O:24])/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH2:8][CH2:7]1)C.[BH4-].[Na+].OS([O-])(=O)=O.[K+]>C(O)C>[Cl:23][C:19]1[CH:18]=[C:17](/[CH:16]=[CH:15]/[C:14]([N:9]2[CH2:10][CH2:11][C:12](=[O:13])[N:6]([CH2:5][CH2:4][OH:3])[CH2:7][CH2:8]2)=[O:24])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 4311764Sodium borohydride2×HCID 68431912{4-[(E)-3-(3-Chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetic acid ethyl ester

Product 1

HCID 684339731-[(E)-3-(3-chloro-phenyl)-acryloyl]-4-(2-hydroxy-ethyl)-[1,4]diazepan-5-oneYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.16 g (5.91 mmol) of {4-[(E)-3-(3-chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetic acid ethyl ester in 30 ml of ethanol was treated at 0° C. with 0.45 g (11.81 mmol) of sodium borohydride in 30 ml of ethanol during 20 min. The reaction was stirred for 21 h at RT, cooled (0° C.) and treated again with 0.45 g (11.81 mmol) of sodium borohydride. After 22 h at RT the reaction neutralized with cold aqueous 10% KHSO4 and extracted with EtOAc (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (EtOAc and then EtOAc/EtOH 1 to 7.5%) to yield 1.50 g (79%) of the title compound as light white foam. MS: 323.1 (MH+, Cl).

Workup

  1. temperaturecooled (0° C.)
  2. extractionextracted with EtOAc (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by flash silica gel column (EtOAc

Sources & evidence

ORD record
ord-dbf76c65999c4a24b9ac88100595eb89
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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