HCID 66732467, compound → HCID 66732334, compound

HRID 1963116Notes

Reaction equation

HRID 1963116 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][CH:10]2[CH:15]=[C:14]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:13]=[CH:12][N:11]2[C:25]([O:27][CH3:28])=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pt](=O)=O>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([CH2:16][O:17][Si:18]([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:19])[CH3:20])[CH2:13][CH2:12][N:11]2[C:25]([O:27][CH3:28])=[O:26])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 66732467HCID 66732467, compound

Product 1

HCID 66732334HCID 66732334, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(4-tert-butylbenzyl)-4-((tert-butyldimethylsilyloxy)methyl)-pyridine-1(2H)-carboxylate (6.5 g, 15.13 mmol) in ethyl acetate (50 mL) was added platinum(IV) oxide (0.07 g, 0.31 mmol). The suspension was hydrogenated at 6 bar H2 atmosphere for 20 h. The mixture was filtered through Celite and the solvents were evaporated to give the product (6.27 g, 96%) as an oil. 1H NMR (400 MHz, cdcl3) δ −0.07-0.18 (m, 6H), 0.77-1.01 (m, 9H), 1.28-1.37 (m, 9H), 1.36-1.87 (m, 4H), 2.58-2.74 (m, 1H), 2.88-3.06 (m, 2H), 3.40-3.55 (m, 3H), 3.60-3.72 (m, 3H), 3.78-4.10 (m, 2H), 7.14-7.32 (m, 4H). MS m/z 434 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvents were evaporated

Sources & evidence

ORD record
ord-c690911e4b1d4e39893a177f31b0ede3
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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