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

HRID 875606Notes

Reaction equation

HRID 875606 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-d295f2a3b3864022939ef1e2bc298129
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

Loading…