HCID 86727106, compound → HCID 71270731, compound

HRID 2175921Notes

Reaction equation

HRID 2175921 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:12][CH2:11][C:10](C(OCC)=O)([C:13]([O:15][C:16](C)(C)[CH3:17])=[O:14])[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 86727106HCID 86727106, compound

Product 1

HCID 71270731HCID 71270731, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 7-tert-butyl 7-ethyl 3-nitro-5,6-dihydro-7H-cyclopenta[b]pyridine-7,7-dicarboxylate (6.2 g, 18.4 mmol) in 30 mL of TFA and 30 mL DCM was stirred at 35° C. for 3 hours then concentrated to dryness. The residue was dissolved in 200 mL of EtOAc and washed with saturated NaHCO3 (2×25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated to afford the title compound.

Workup

  1. concentrationthen concentrated to dryness
  2. dissolutionThe residue was dissolved in 200 mL of EtOAc
  3. washwashed with saturated NaHCO3 (2×25 mL) and brine (25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d7656fad65084f74b50663ead883a7ff
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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