HCID 66731958, compound → HCID 66731768, compound

HRID 1963341Notes

Reaction equation

HRID 1963341 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)[CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=1)[C:12]([O:14][CH3:15])=[O:13])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pt](=O)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)[CH2:8][CH:9]1[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 66731958HCID 66731958, compound

Product 1

HCID 66731768HCID 66731768, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(3,5-di-tert-butylbenzyl)isonicotinate (3.538 g, 10.42 mmol) was dissolved in acetic acid (30 mL) and platinum(IV) oxide (0.118 g, 0.52 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 5 h 45 min. The catalyst was filtered off and washed with MeOH and the eluate evaporated. DCM and 10% K2CO3 were added and the phases separated. The organic layer was washed with brine, passed through a phase separator and evaporated to yield crude methyl 2-(3,5-di-tert-butylbenzyl)piperidine-4-carboxylate (3.80 g, 106%) as a beige oil. MS m/z 346 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. additionDCM and 10% K2CO3 were added
  5. customthe phases separated
  6. washThe organic layer was washed with brine
  7. customevaporated

Sources & evidence

ORD record
ord-7d1833d027b9445fb85c9133f84ee7cc
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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