methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)pyridine-1(2H)-carboxylate → Methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)piperidine-1-carboxylate

HRID 1963263Notes

Reaction equation

HRID 1963263 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pt](=O)=O>[Si:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66734557methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)pyridine-1(2H)-carboxylate

Product 1

HCID 66731995Methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)-pyridine-1(2H)-carboxylate (3.63 g, 9.87 mmol) in ethyl acetate (60 mL) was platinum (IV) oxide (224 mg, 1 mmol) added. Hydrogenated at 6 bar in a Büchi hydrogenator for 3.5 h. The catalyst was filtered off and the filtrate evaporated to yield methyl 4-((tert-butyl-dimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)piperidine-1-carboxylate (3.62 g, 99%) as a colourless oil. MS m/z 372 (M+H)+

Workup

  1. additionadded
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-726031917d164549961e667c14dc48b7
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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