Formaldehyde formic acid → 4-methyl-3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

HRID 1416612ノート

反応式

HRID 1416612 の反応式
[ClH:1].Cl.[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[CH:17](O)=O.C=O>>[ClH:1].[ClH:1].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17]

参加物

3

反応物 2

HCID 18761834Formaldehyde formic acidHCID 213097024-methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine dihydrochloride

生成物 1

HCID 675852194-methyl-3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

実験手順

To a 330 mg sample of 4methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine (from Example 27 above) was added a solution of formic acid/ formaldehyde (1:2,2 mL). The mixture was heated at reflux for 5 hours, and the volatiles were removed by evaporation. 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 to afford 295 mg of the title compound. MS (DCI/NH3) m/e: 207 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.17 (s, 1H), 8.12 (d, J=5.5 Hz, 1H), 7.06 (d, J=5.5 Hz, 1H), 4.07 (dd, J=3.3, 10.6 Hz, 1H), 3.98 (dd, J=7.4, 10.6 Hz, 1H), 3.15-3.08 (m, 1H), 2.76-2.68 (m, 1H), 2.53 (s, 3H), 2.38-2.25 (m, 1H), 2.26 (s, 3H), 2.12-1.67 (m, 4H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. customthe volatiles were removed by evaporation
  4. dissolutionThe residue was dissolved in 1 mL of 20% NaOH
  5. extractionThe solution was extracted with CH2Cl2 (3X)
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography over silica gel

出典と根拠

ORDレコード
ord-dd788ce24ee74b5fa2908fdbe7b25643
出典データセット
uspto-grants-1999_06
特許番号
US05914328

反応ノート

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