Trimethyl orthoformate → HCID 69312194, compound

HRID 750914Notes

Reaction equation

HRID 750914 reaction equation
[F:1][C:2]1([F:18])C(=O)[CH2:6][CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:3]1.[CH3:19][O:20][CH:21](OC)[O:22][CH3:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:19][O:20][C:21]1([O:22][CH3:23])[CH2:6][CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:3][C:2]1([F:1])[F:18]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 69315461HCID 69315461, compound

Product 1

HCID 69312194HCID 69312194, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

The mixture of 4-(3,3-difluoro-4-oxo-piperidin-1-yl)-nitrobenzene (25 mmol), trimethylorthoformate (51 mmol), p-toluene-sulphonic acid monohydrate (27 mmol) in methanol was heated at 45° C. for 24 hours. Solvent was removed and residual mass was taken into ethyl acetate and saturated sodium bicarbonate solution mixture. The organic layer was dried and removal of the solvent afforded title compound as a solid in 84% yield.

Workup

  1. customSolvent was removed
  2. customThe organic layer was dried
  3. customremoval of the solvent

Sources & evidence

ORD record
ord-d6857387597e4ee8aed5f3db64d2c2dc
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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