Thiomorpholine → 1,1,1-Trifluoro-4(5-fluoro-2-methoxyphenyl)-4-methyl-2-thiomorpholin-4-ylmethylpentan-2-ol

HRID 2105985Notes

Reaction equation

HRID 2105985 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[NH:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1>CN(C)C=O.C(OCC)C>[F:14][C:13]([F:16])([F:15])[C:10]([CH2:12][N:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1)([OH:11])[CH2:9][C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:19][CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 67164ThiomorpholineHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 104532961,1,1-Trifluoro-4(5-fluoro-2-methoxyphenyl)-4-methyl-2-thiomorpholin-4-ylmethylpentan-2-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (see Example 1) (130 mg) and thiomorpholine (84.6 μL) in dimethylformamide (1 μL) was heated at 100° C. for 15 hours. The resulting mixture was diluted with diethyl ether, washed with water and brine, dried over sodium sulfate, filtered, and the volatiles removed in vacuo. The residue was purified by silica gel column chromatography using 2% EtOAc-hexanes as the eluent. The product-rich fractions were concentrated in vacuo to provide the title compound as a clear oil (161 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe volatiles removed in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. concentrationThe product-rich fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-2553ffd9f11c47ecb6e10b1c9e799b20
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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