HCID 57652009, compound → tert-Butyl methylcarbamate

HRID 1641790Notes

Reaction equation

HRID 1641790 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7](C)[CH:8]1CCN(C2C=CC([N+]([O-])=O)=CN=2)CC1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 57652009HCID 57652009, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 527635tert-Butyl methylcarbamateYield 226.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl (5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-carbamic acid tert-butyl ester (1.4 g, 4.2 mmol) in ethyl acetate (5 mL) in the presence of 10% palladium on carbon (0.15 g) was shaken under 40 psi of hydrogen at room temperature for 2 h. The reaction mixture was filtered through a plug of celite and the filtration pad was washed with ethyl acetate. The combined washings were concentrated and dried to give 5′-amino-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-methyl-carbamic acid tert-butyl ester (1.25 g, 98%) as a brown solid. This material was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washthe filtration pad was washed with ethyl acetate
  3. concentrationThe combined washings were concentrated
  4. customdried

Sources & evidence

ORD record
ord-fa43482ac1e047dd82feb47bd57be853
Source dataset
uspto-grants-2012_02
Patent number
US08115011B2

Reaction notes

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