Tetrahydrofuran → HCID 70110585, compound

HRID 1378385Notes

Reaction equation

HRID 1378385 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([F:14])([F:13])[F:12])[CH2:9][N:8]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:7]1)=O)C.O1CCCC1.[OH-].[Na+]>S([O-])([O-])(=O)=O.[Na+].[Na+].CCCCCC.C(OCC)(=O)C>[CH2:15]([N:8]1[CH2:9][C@@H:10]([C:11]([F:14])([F:12])[F:13])[C@H:6]([CH2:4][OH:3])[CH2:7]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11066560HCID 11066560, compound

Product 1

HCID 70110585HCID 70110585, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 24436Sodium SulfateCatalystHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixed solution of 2.86 g (9.50 mmol) of trans-1-benzyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester and 15 ml of absolute tetrahydrofuran is added dropwise to the above suspension over 40 minutes on cooling with ice. After stirring at 0° C. for 1.5 hours, the excess reagent is decomposed by adding several drops of sodium sulfate (decahydrate) and 2N sodium hydroxide. Insoluble matter is removed by filtration under reduced pressure. The filtrate is concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (elusion solvent; n-hexane/ethyl acetate (5/1→5/2 (by volume, hereinafter the same))) to give 2.25 g of the objective substance as a colorless powder (yield 91.4%).

Workup

  1. temperatureon cooling with ice
  2. customInsoluble matter is removed by filtration under reduced pressure
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (elusion solvent

Sources & evidence

ORD record
ord-df4b01bf1af2421ea0af237e1956bac7
Source dataset
uspto-grants-1997_09
Patent number
US05668147

Reaction notes

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