HCID 22258740, compound → HCID 22258804, compound

HRID 412273Notes

Reaction equation

HRID 412273 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:3]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:3]=1

Participants

4

Reactant 1

HCID 22258740HCID 22258740, compound

Product 1

HCID 22258804HCID 22258804, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[2-amino-6-[2-(benzyloxy)phenyl]-3-(hydroxymethyl)-4-pyridinyl]-1-piperidinecarboxylate (0.900 g, 1.838 mmol) in methylene chloride (20 mL) was added manganese (IV) oxide (3.20 g, 36.8 mmol). After stirred at room temperature for 40 min, the mixture was filtered to remove the manganese salt. The filtrate was concentrated under reduced pressure. The resulting solid was purified by recrystallization from a mixture of ethyl acetate and hexane to give tert-butyl 3-[2-amino-6-[2-(benzyloxy)phenyl]-3-formyl-4-pyridinyl]-1-piperidinecarboxylate. (0.651 g, yield; 73%)

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the manganese salt
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resulting solid was purified by recrystallization from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-8fb877b2d35a4c239b8cbe49699557b0
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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