Sodium hydride → 5-(2,6-Dimethoxyphenyl)-4-(4-(trifluoromethoxy)benzyl)-morpholin-3-one

HRID 594418Notes

Reaction equation

HRID 594418 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]([N:7]([CH:20]([C:23]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=1[O:31][CH3:32])[CH2:21][OH:22])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)=[O:6]>CN(C=O)C>[CH3:32][O:31][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:23]=1[CH:20]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[C:5](=[O:6])[CH2:4][O:22][CH2:21]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 690820062-chloro-N-(1-(2,6-dimethoxyphenyl)-2-hydroxyethyl)-N-(4-(trifluoromethoxy)benzyl)-acetamide

Product 1

HCID 690827665-(2,6-Dimethoxyphenyl)-4-(4-(trifluoromethoxy)benzyl)-morpholin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A cooled (−25° C.) mixture of NaH (60% dispersion in mineral oil; 1 mg; 0.025 mmol) in anh. DMF (1 ml) was treated dropwise with a solution of 2-chloro-N-(1-(2,6-dimethoxyphenyl)-2-hydroxyethyl)-N-(4-(trifluoromethoxy)benzyl)acetamide (10 mg; 0.022 mmol) in anh. DMF (1 ml). The resulting mixture was further stirred at rt, under nitrogen, for 30 min. The mixture was then filtered, and the obtained filtrate was directly purified by preparative HPLC affording 5-(2,6-dimethoxyphenyl)-4-(4-(trifluoromethoxy)benzyl)-morpholin-3-one as a yellow oil. LC-MS (conditions E): tR=0.79 min.; [M+H]+: 412.06 g/mol.

Workup

  1. temperatureA cooled
  2. filtrationThe mixture was then filtered
  3. customthe obtained filtrate was directly purified by preparative HPLC

Sources & evidence

ORD record
ord-3b9f1f6b70d74c1793db9bee860299f9
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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