HCID 21309676, compound → HCID 21309696, compound

HRID 1416642Notes

Reaction equation

HRID 1416642 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>C1COCC1>[OH:9][CH2:8][C@H: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

3

Reactant 1

HCID 21309676HCID 21309676, compound

Product 1

HCID 21309696HCID 21309696, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 g (4.2 mmol) sample of 3-((-1-methyl-4-hydroxymethyl-5-oxo-2(S)-pyrrolidinyl)methoxy)pyridine, from step 48a above, was dissolved in 15 mL of anhydrous THF, 12.7 mL of BH3 was added, and the mixture was heated at reflux for 2.5 hours. The reaction was quenched with methanol, the solvent was evaporated, and the residue was dissolved in anhydrous ethanol. Cesium fluoride was added, and the resultant solution was stirred under reflux for 16 hr. Evaporation of the solvent and purification of the residue on a silica gel column, eluting with 100:8 to 10: 1 chloroform:methanol gave 600 mg of the title compound as a mixture of cis and trans product.

Workup

  1. addition12.7 mL of BH3 was added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2.5 hours
  4. customThe reaction was quenched with methanol
  5. customthe solvent was evaporated
  6. dissolutionthe residue was dissolved in anhydrous ethanol
  7. additionCesium fluoride was added
  8. temperatureunder reflux for 16 hr
  9. customEvaporation of the solvent and purification of the residue on a silica gel column
  10. washeluting with 100:8 to 10: 1 chloroform

Sources & evidence

ORD record
ord-bcbc15bb97d645479d35aca76428304a
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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