Potassium tert-butoxide → HCID 58155298, compound

HRID 1929472Notes

Reaction equation

HRID 1929472 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]([NH:14][C:15](=[O:18])[CH2:16]Cl)([CH:11]2[CH2:13][CH2:12]2)[CH2:9][OH:10])[CH:7]=1.CC(C)([O-])C.[K+]>C(O)CCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2([CH:11]3[CH2:13][CH2:12]3)[NH:14][C:15](=[O:18])[CH2:16][O:10][CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58155316HCID 58155316, compound

Product 1

HCID 58155298HCID 58155298, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In an analogous manner to that described for the preparation of Building block A [e)], the cyclization of (RS)-N-[1-(5-bromo-2-fluoro-phenyl)-1-cyclopropyl-2-hydroxy-ethyl]-2-chloro-acetamide with potassium tert-butoxide in tent-butanol at room temperature overnight yielded the (RS)-5-(5-bromo-2-fluoro-phenyl)-5-cyclopropyl-morpholin-3-one as a yellow oil (2.146 g, 88% of theory). Mass (calculated) C13H13BrFNO2 [314.153]; (found) [M+H]+=314, [M+2-H]+=316.

Sources & evidence

ORD record
ord-c7cb8ec87d25464da8d3c5afae97b258
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

Loading…