tert-butyl 4-(2-(3-methoxy-3-oxopropyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → HCID 68160489, compound

HRID 537354Notes

Reaction equation

HRID 537354 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=1>CCO.CC(O)=O.O=[Pt]=O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 67111238tert-butyl 4-(2-(3-methoxy-3-oxopropyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 68160489HCID 68160489, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

23 (310 mg, 0.90 mmol) was dissolved in EtOH/AcOH (4 mL/4 mL). The solution was degassed with Ar for 2 min. PtO2 (61 mg, 0.27 mmol) was added to the mixture and H2 was bubbled in for 2 min. The reaction was stirred under a H2 balloon overnight. The reaction mixture was filtered through Celite and was concentrated to yield tert-butyl 4-(2-(3-methoxy-3-oxopropyl)phenyl)piperidine-1-carboxylate. LC/MS RT (5 min method)=2.47 min. Mass observed: 248.21 (M-Boc+H).

Workup

  1. customThe solution was degassed with Ar for 2 min
  2. customwas bubbled in for 2 min
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-9b6a643390864f4eba81b2e2ef4581a2
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

Loading…