Formaldehyde → HCID 10263121, compound

HRID 1416621Notes

Reaction equation

HRID 1416621 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>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

4

Reactant 2

HCID 712FormaldehydeHCID 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% paraformaldehyde 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 (3X), 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 (3X)
  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-09ca2023bf134d62b9d6cece63cae712
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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