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

HRID 1041960Notes

Reaction equation

HRID 1041960 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23][CH2:22]3)[CH:15]=[CH:16][CH:17]=2)[N:12]=1)CO>C(Cl)Cl>[CH:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:23][CH2:22]3)[CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[O:7]

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-b1ef341be7ae4bb190877c97f54aeb3a
Source dataset
uspto-grants-2013_10
Patent number
US08557809B2

Reaction notes

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