Trifluoroacetic anhydride → HCID 67064808, compound

HRID 2045762Notes

Reaction equation

HRID 2045762 reaction equation
O[CH2:2][CH:3]([CH:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH:7]1[CH3:13])[C:4]#[N:5].N12CCCC=C1CCCCN2.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:13][CH:7]1[CH2:8][C:9]([CH3:12])([CH3:11])[CH2:10][CH:6]1[C:3](=[CH2:2])[C:4]#[N:5]

Participants

6

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 67064815HCID 67064815, compound

Product 1

HCID 67064808HCID 67064808, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The 3-hydroxy-2-(2,4,4-trimethylcyclopentyl)propanenitrile is placed in dichloromethane at 10° C. under an inert atmosphere. 2.2 eq. of DBU (diazabicyclo[5.4.0]undec-7-ene) and a few crystals of DMAP (4-dimethylaminopyridine) are added thereto, followed, dropwise, by 1.2 eq. of trifluoro-acetic anhydride. The reaction medium is stirred at ambient temperature overnight and is then poured onto water. The aqueous phase is extracted once with dichloromethane. The combined organic phases are washed with water. After drying over magnesium sulfate, filtering through paper and evaporating the solvent, the crude product, obtained in the form of two diastereomers in proportions of 70:30, is distilled under reduced pressure.

Workup

  1. additionis then poured onto water
  2. extractionThe aqueous phase is extracted once with dichloromethane
  3. washThe combined organic phases are washed with water
  4. dry with materialAfter drying over magnesium sulfate
  5. filtrationfiltering through paper
  6. customevaporating the solvent

Sources & evidence

ORD record
ord-d3a0c6cee23f45ef9913ec7d428766f6
Source dataset
uspto-grants-2013_11
Patent number
US08592360B2

Reaction notes

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