Sodium periodate → Tert-butyl (1-(2-formylquinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 339673Notes

Reaction equation

HRID 339673 reaction equation
I([O-])(=O)(=O)=O.[Na+].[C:7]([O:11][C:12](=[O:35])[NH:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[C:28]([CH:31]([OH:34])CO)[CH:27]=[CH:26]3)[CH2:17][CH2:16]1)([CH3:10])([CH3:9])[CH3:8]>C(Cl)Cl>[C:7]([O:11][C:12](=[O:35])[NH:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[C:28]([CH:31]=[O:34])[CH:27]=[CH:26]3)[CH2:17][CH2:16]1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 86654344Tert-butyl (1-(2-(1,2-dihydroxyethyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 86654345Tert-butyl (1-(2-formylquinolin-8-yl)piperidin-4-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium periodate (0.34 mL, 0.22 mmol was added drop-wise to a slurry of silica gel (0.4 g) in DCM (3 mL)). The reaction was stirred for 10 minutes. tert-Butyl(1-(2-(1,2-dihydroxyethyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (74 mg, 0.18 mmol) in DCM (2 mL) was then added to the slurry and the reaction was stirred for 30 minutes. The reaction was filtered and the collected solids were washed with DCM (20 mL). The filtrate was concentrated to give the crude product.

Workup

  1. stirringthe reaction was stirred for 30 minutes
  2. filtrationThe reaction was filtered
  3. washthe collected solids were washed with DCM (20 mL)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d4c98e09ba2a432798e579599351b52d
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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