Methyl trifluoromethyl ketone → HCID 67776705, compound

HRID 633706Notes

Reaction equation

HRID 633706 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[F:28][C:29]([F:34])([F:33])[C:30](=O)[CH3:31]>C1(C)C=CC=CC=1>[CH3:31][C@@:30]1([C:29]([F:34])([F:33])[F:28])[NH:10][CH:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:8][O:9]1

Participants

5

Reactant 3

HCID 9871Methyl trifluoromethyl ketoneHCID 924662-Amino-2-phenylethanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 67776705HCID 67776705, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

25 g (180 mmol) of (R)-phenylglycinol and then 4 g (16 mmol) of pyridinium para-toluenesulfonate are added to a solution of 25.8 g (230 mmol) of trifluoroacetone in 200 mL of toluene in a three-necked flask on which is mounted Dean-Stark apparatus. The mixture obtained is then heated at 110° C. for 5 hours. After cooling, the reaction mixture is concentrated under reduced pressure. The residue obtained is purified by filtration on silica (eluent: dichloromethane) to give 35.10 g of (R)-2-methyl-4-phenyl-2-trifluoromethyloxazolidine in the form of a colorless liquid, the characteristics of which are as follows:

Workup

  1. customThe mixture obtained
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. customThe residue obtained
  5. filtrationis purified by filtration on silica (eluent: dichloromethane)

Sources & evidence

ORD record
ord-0bb3c6082a2841f4adabfc6e5f59170e
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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