tert-Butyl 1H-pyrrolo[2,3-c]pyridine-1-carboxylate → tert-Butyl octahydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

HRID 919630Notes

Reaction equation

HRID 919630 reaction equation
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H][H]>CC(O)=O.C(OCC)(=O)C.O=[Pt]=O>[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]2[CH2:6][NH:7][CH2:8][CH2:9][CH:4]2[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 22646996tert-Butyl 1H-pyrrolo[2,3-c]pyridine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 54595540tert-Butyl octahydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylateYield 101.8%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 1H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.5 g, 2.3 mmol) in AcOH (15 mL) was added PtO2 (0.25 g, 1.1 mmol). The mixture was treated with an atmosphere of hydrogen atmosphere (60 psi) and stirred for 12 h at rt. The suspension was filtered through a pad celite and concentrated in vacuo to afford a residue. The crude material was diluted with ethyl acetate (50 mL) and washed with sat. NaHCO3 (100 mL), the organic phase was separated, dried (Na2SO4) filtered and concentrated in vacuo to afford the title compound (0.53 g, 99% yield). 1H NMR (400 MHz, CDCl3) δ=6.07-5.58 (m, 1H), 4.03-3.68 (m, 1H), 3.57-3.22 (m, 3H), 3.05-2.66 (m, 2H), 2.49-2.19 (m, 1H), 1.96 (s, 4H), 1.77-1.64 (m, 1H), 1.45 (s, 9H). LC/MS (m/z): calc; d. For C12H22N2O2 (M+1H) 227. found 227.2.

Workup

  1. filtrationThe suspension was filtered through a pad celite
  2. concentrationconcentrated in vacuo
  3. customto afford a residue
  4. washwashed with sat. NaHCO3 (100 mL)
  5. customthe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b20bc758dff6405086370c910e68e696
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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