Methanol → HCID 54356602, compound

HRID 1419576Notes

Reaction equation

HRID 1419576 reaction equation
B.O1CCCC1.[C:7]1([NH:13][C:14]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:7]1([NH:13][CH2:14][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 51204633HCID 51204633, compound

Product 1

HCID 54356602HCID 54356602, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (1.0M in tetrahydrofuran, 57 mL, 57 mmol) was added to a stirred, cooled (0° C.) solution N-phenyl-1-t-butoxycarbonylpiperidine-4-carboxamide (5.78 g, 19 mmol) in tetrahydrofuran (95 mL) and the mixture was stirred at room temperature for 18 h. Methanol (10 mL) was added and the solvent was evaporated under reduced pressure. Potassium carbonate (13.13 g, 95 mmol) and methanol (150 mL) were added and the mixture was heated under reflux for 1 h. The mixture was cooled and the solvent was evaporated under reduced pressure. Water (100 mL) was added and the mixture was extracted with dichloromethane (3×100 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/Hexane (20:80) to give the title compound as a colorless solid (5.08 g, 92%), δH (250 MHz, CDCl3) 7.18 (2H, t, J 7.6 Hz), 6.69 (1H, t, J 7.6 Hz), 6.59 (2H, d, J 7.6 Hz), 4.14 (2H, m), 3.73 (1H, br s), 3.03 (2H, d, J 6.2 Hz), 2.69 (2H, m), 1.79-1.55 (3H, m), 1.46 (9H, s), and 1.20 (2H, m).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 h
  4. temperatureThe mixture was cooled
  5. customthe solvent was evaporated under reduced pressure
  6. additionWater (100 mL) was added
  7. extractionthe mixture was extracted with dichloromethane (3×100 mL)
  8. dry with materialThe combined organic fractions were dried (MgSO4)
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by flash column chromatography on silica gel
  11. washeluting with EtOAc/Hexane (20:80)

Sources & evidence

ORD record
ord-7639be09fe1c401e8624b8c577db6773
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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