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

HRID 226384Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[C:3]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[N:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl (3R)-3-{[3-chloro-5-(hydroxymethyl)-2-pyridinyl]amino}-1-piperidinecarboxylate (10.0 g) and MnO2 (25.4 g) in CHCl3 (200 ml) was stirred at 60° C. for 3.5 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-piperidinecarboxylate (9.08 g).

Workup

customAfter removal of the insoluble material
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-85fcc967627b433c97b11083bf961a89
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557127B2

Reaction notes

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