Butylate → (R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-morpholin-3-one hydrochloride

HRID 1929466Notes

Reaction equation

HRID 1929466 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C@:8]([NH:12][C:13](=[O:16])[CH2:14][Cl:15])([CH3:11])[CH2:9][OH:10])[CH:7]=1.[K].CCSC([N:24](CC(C)C)CC(C)C)=O>[Pd]>[ClH:15].[NH2:24][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

5

Reactant 3

HCID 16181ButylateHCID 5462222PotassiumHCID 66931512(R)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

Product 1

HCID 66931442(R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-morpholin-3-one hydrochloride

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In close analogy to the reaction sequence described for the preparation of Building block C, the cyclization of the (R)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide with potassium tent-butylate, followed by the palladium-catalyzed amination, and, finally, by the hydrolysis yielded the (R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-morpholin-3-one hydrochloride as a light yellow solid. Mass (calculated) C11H14ClN2O2 [260.698]; (found) [M+H]+=225.

Workup

  1. customIn close analogy to the reaction sequence described for the preparation of Building block C

Sources & evidence

ORD record
ord-51e817badd2c410c9838301e113970cd
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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