Methanol → HCID 53783690, compound

HRID 617322Notes

Reaction equation

HRID 617322 reaction equation
[CH3:1][N:2]1[C:6](=O)[CH:5]([CH2:8][OH:9])[CH2:4][C@H:3]1[CH2:10][O:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[H]1[BH2][H][BH2]1.CO>C1COCC1>[OH:9][CH2:8][CH:5]1[CH2:6][N:2]([CH3:1])[C@H:3]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 887MethanolHCID 21309676HCID 21309676, compound

Product 1

HCID 53783690HCID 53783690, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 401 mg (2 mmol) sample of 3-(1-methyl4-hydroxymethyl-5-oxo-2(S)-pyrrolidinylmethoxy)pyridine, from step 48a above, was dissolved in 6 mL of THF and 6 mL of 1M B2H6 was added. The reaction mixture was heated at reflux for 2 hours, then stirred at room temperature for 15 minutes after methanol was added. The solvent was removed under pressure, and the residue was dissolved in 4 mL of ethanol. The this solution was added 251 mg of CsF, and the reaction mixture was heated at reflux for 16 hours. The solvent was removed, and the residue was purified on a column of silica gel, eluting with 100:5 to 10:1 chloroform:methanol 78 mg of a mixture of cis and trans product. cis compound: MS (DCI/NH3) m/e: 223 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.32 (m, 1H), 8.23 (t, 1H, J=3 Hz), 7.21 (m, 1H), 4.16-3.94 (m, 2H), 3.77-3.54 (m, 2H), 3.09-3.01 (m, 1H), 2.88-2.64 (m, 1H), 2.58-2.47 (m, 1H), 2.46 (m, 1H), 2.46 (s, 1H), 2.38-2.29 (m, 1H), 1.98-1.81 (m, 1H). trans compound: MS (DCI/NH3) m/e: 223 (M+H)+. 1H NMR (CDCl3, 300 MHz) d: 8.33 (m, 1H), 8.23 (m, 1H), 7.23 (m, 1H), 4.20-3.96 (m, 2H), 3.74-3.59 (m, 2H), 3.42-3.26 (m, 1H), 2.97-2.83 (m, 1H), 2.54 (s, 1H), 2.48-2.23 (m, 1H), 2.04-1.80 (m, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. additionwas added
  4. customThe solvent was removed under pressure
  5. dissolutionthe residue was dissolved in 4 mL of ethanol
  6. additionThe this solution was added 251 mg of CsF
  7. temperaturethe reaction mixture was heated
  8. temperatureat reflux for 16 hours
  9. customThe solvent was removed
  10. customthe residue was purified on a column of silica gel
  11. washeluting with 100:5 to 10:1 chloroform
  12. additionmethanol 78 mg of a mixture of cis and trans product

Sources & evidence

ORD record
ord-5fa5c30f9ec44f709f0b55cff5d65de2
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

Loading…