Reaction #1121799

Reaction equation

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

EtOH

→

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

Yield 95.5%

Solvents

AcOH

Conditions

Workup

1. 1
   ConcentrationThe reaction was then concentrated
2. 2
   workup.DISSOLUTIONthe crude oil was dissolved in DCM
3. 3
   workup.ADDITIONpoured into saturated Na2CO3
4. 4
   Extractionextracted into DCM
5. 5
   OtherThe combined organic fractions were dried
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

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.

Source