Methanol → HCID 118037920, compound

HRID 2272495Notes

Reaction equation

HRID 2272495 reaction equation
[CH2:1]([C:3]1[C:4](=[O:30])[N:5]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH:6]=[CH:7][C:8]=1OS(C(F)(F)F)(=O)=O)[CH3:2].C(N(CC)CC)C.[CH3:38][OH:39].[C]=O.CN([CH:45]=[O:46])C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([N:5]2[CH:6]=[CH:7][C:8]([C:38]([O:46][CH3:45])=[O:39])=[C:3]([CH2:1][CH3:2])[C:4]2=[O:30])[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 118037594HCID 118037594, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 118037920HCID 118037920, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

A mixture of tert-butyl 4-(3-ethyl-2-oxo-4-(((trifluoromethyl)sulfonyl)oxy)pyridin-1(2H)-yl)piperidine-1-carboxylate (1.14 g), triethylamine (0.699 mL), methanol (3.05 mL), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.184 g), and DMF (12.5 mL) was stirred at 90 C for 4 hours in a carbon monooxide atmosphere of 0.5 MPa. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The obtained organic layer was washed with saturated saline twice and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to obtain the title compound (0.798 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe obtained organic layer was washed with saturated saline twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cf934c268edc486da59063d09db34382
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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