Potassium tert-butoxide → 5-(5-Bromo-2-fluorophenyl)-5-methylmorpholin-3-one

HRID 593343Notes

Reaction equation

HRID 593343 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]([NH:12][C:13](=[O:16])[CH2:14]Cl)([CH3:11])[CH2:9][OH:10])[CH:7]=1.CC([O-])(C)C.[K+]>ClCCl.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]2([CH3:11])[NH:12][C:13](=[O:16])[CH2:14][O:10][CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58155286(RS)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

Product 1

HCID 581552625-(5-Bromo-2-fluorophenyl)-5-methylmorpholin-3-one

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The cyclization of the (RS)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide [preparation of building block B e)] with potassium tert-butylate yielded, after chromatography on silica gel using a gradient of dichloromethane/methanol=100/0 to 75/25 as the eluent, the title compound as a white solid. Mass (calculated) C1H11BrFNO2 [288.118]; (found) [M+H]+=288 and [M+2+H]+=290.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-aa3fc57331df40fc9a5ace7e13bb2ea6
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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