tert-butyl (3R)-3-{[3-chloro-5-(hydroxymethyl)-2-pyridinyl]amino}-1-pyrrolidinecarboxylate → tert-butyl (3R)-3-[(3-chloro-5-formyl-2-pyridinyl)amino]-1-pyrrolidinecarboxylate

HRID 226425Notes

Reaction equation

HRID 226425 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1>CCOC(C)=O.O=[Mn]=O>[Cl:1][C:2]1[C:3]([NH:10][C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)=[N:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

4

Reactant 1

HCID 86603728tert-butyl (3R)-3-{[3-chloro-5-(hydroxymethyl)-2-pyridinyl]amino}-1-pyrrolidinecarboxylate

Product 1

HCID 86603729tert-butyl (3R)-3-[(3-chloro-5-formyl-2-pyridinyl)amino]-1-pyrrolidinecarboxylateYield 100.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl (3R)-3-{[3-chloro-5-(hydroxymethyl)-2-pyridinyl]amino}-1-pyrrolidinecarboxylate (0.95 g) and MnO2 (3.02 g) in AcOEt (30 ml) was refluxed under stirring for 1.5 hours. After removal of the insoluble material, and the solvent was evaporated in vacuo to give tert-butyl (3R)-3-[(3-chloro-5-formyl-2-pyridinyl)amino]-1-pyrrolidinecarboxylate (0.95 g).

Workup

  1. temperaturewas refluxed
  2. customAfter removal of the insoluble material
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fca4f9c2dfab42f2a1d7c0f0faaf07f2
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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