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

HRID 875688Notes

Reaction equation

HRID 875688 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 shaken at 50 PSI under H2 for 8 hours. The reaction was then concentrated. The crude oil was dissolved in DCM, poured into saturated Na2CO3 and extracted into DCM. The organic fraction was dried, filtered, and concentrated to give the product as an oil, tert-butyl octahydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.99 g, 95.5% yield).

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 organic fraction was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d83d6102f0814f4a8965685716d66bec
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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