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

HRID 408121Notes

Reaction equation

HRID 408121 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.CCO>O=[Pt]=O.CC(O)=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

5

Reactant 2

HCID 702EthanolHCID 22646996tert-Butyl 1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Product 1

HCID 54595540tert-Butyl octahydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylateYield 95.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

tert-Butyl 1H-pyrrolo[2,3-c]pyridine-1-carboxylate (1.0 g, 4.58 mmol) and PtO2 (0.208 g, 0.916 mmol) were placed in 1:1 EtOH:AcOH (10 mL) and hydrogenated at 50 PSI of H2 for 8 hours (Parr shaker). The reaction was then concentrated, and the crude oil was dissolved in DCM and poured into saturated Na2CO3 and extracted into DCM. The combined organic fractions were dried, filtered, and concentrated to give tert-butyl octahydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.99 g, 95% yield) as an oil.

Workup

  1. concentrationThe reaction was then concentrated
  2. dissolutionthe crude oil was dissolved in DCM
  3. additionpoured into saturated Na2CO3
  4. extractionextracted into DCM
  5. customThe combined organic fractions were dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b500a58117ac40e980df555d490f4c5a
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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