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

HRID 712425Notes

Reaction equation

HRID 712425 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 113.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of tert-butyl 1H-pyrrolo[2,3-c]pyridine-1-carboxylate (1.85 g) and a catalytic amount of PtO2 in the mixture solvent of EtOH (10 mL) and AcOH (10 mL) was heated overnight under H2 (2.0 MPa). The reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to afford the product as viscous liquid (2.18 g, 100.00%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-9f3a1e671cc6476f842471b6ab1c6637
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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