HCID 10615059, compound → HCID 10263121, compound

HRID 617328Notes

Reaction equation

HRID 617328 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=O)(C)(C)C>C(O)=O>[Cl:21][C:18]1[N:17]=[CH:16][C:15]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH3:6])=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 10615059HCID 10615059, compound

Product 1

HCID 10263121HCID 10263121, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 625 mg sample of 3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)-6-chloropyridine, prepared as in Example 45a, was treated with 2 mL of 37% parafornaldehyde and 1 mL of formic acid at reflux for 16 hours. The volatiles were removed by evaporation, and the residue was dissolved in 1 mL of 20% NaOH. The solution was extracted with CH2Cl2 (3×), then the organic layer was dried (Na2SO4) and concentrated. The crude product was purified by chromatography over silica gel, eluting with 100:1 chloroform:methanol to afford 439 mg of the title compound. MS (DCI/NH3) m/e: 227/229 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.09 (dd, J=2.1, 2.1 Hz, 1H), 7.24-7.21 (m, 2H), 4.02 (dd, J=11.0, 3.0 Hz, 1H), 3.93 (dd, J=11.0, 5.8 Hz, 1H), 3.21-3.10 (m, 1H), 2.76-2.64 (m, 1H), 2.51 (s, 3H), 2.40-2.28 (m, 1H), 2.12-1.98 (m, 1H), 1.97-1.68 (m, 4H).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe volatiles were removed by evaporation
  3. dissolutionthe residue was dissolved in 1 mL of 20% NaOH
  4. extractionThe solution was extracted with CH2Cl2 (3×)
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography over silica gel
  8. washeluting with 100:1 chloroform

Sources & evidence

ORD record
ord-f06f5b03aa2149b3a961cd9ddc83e0ef
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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