tert-butyl 4-methylpyridin-3-ylcarbamate → HCID 45092184, compound

HRID 919615Notes

Reaction equation

HRID 919615 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]>C(O)(=O)C.O=[Pt]=O>[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 1

HCID 11063649tert-butyl 4-methylpyridin-3-ylcarbamate

Product 1

HCID 45092184HCID 45092184, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Tert-butyl 4-methylpyridin-3-ylcarbamate (200 mg, 0.96 mmol) was dissolved in glacial acetic acid (5 mL) and treated with PtO2 (200 mg, 1:1 w/w) under an atmosphere of hydrogen. The reaction mixture was stirred at rt for 15 h. The reaction mixture was then filtered through a pad of Celite. The filtrate was neutralized with solid NaHCO3, and extracted with EtOAc (5×50 mL). The organic layer was dried over Na2SO4, concentrated in vacuo to yield the titled compound (160 mg, 77%), which was used for next step without further purification. 1H NMR (400 MHz, CDCl3): δ 4.38-4.21 (m, 1H), 3.32-2.81 (m, 3H), 2.63-2.49 (m, 2H), 2.41-2.32 (m, 1H), 1.78-1.56 (m, 3H), 1.59 (s, 9H), 1.05 and 0.98 (2d, J=6.8 Hz, 3H). ES-MS: m/z [M+1]=215.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite
  2. extractionextracted with EtOAc (5×50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b640654f644d46f2871b382be1680138
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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