Pyridine → HCID 86726793, compound

HRID 1499570Notes

Reaction equation

HRID 1499570 reaction equation
N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:29]([O:36][C:37]([N:39]1[CH2:44][CH:43]([CH3:45])[CH:42]([OH:46])[CH:41]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:40]1)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:29]([O:36][C:37]([N:39]1[CH2:44][CH:43]([CH3:45])[C:42](=[O:46])[CH:41]([NH:47][C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49])[CH2:40]1)=[O:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86726794HCID 86726794, compound

Product 1

HCID 86726793HCID 86726793, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.8 mL, 10 mmol) and Dess-Martin periodinane (1.8 g, 4.4 mmol) were added to a stirred solution of benzyl-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-5-methylpiperidine-1-carboxylate (1.22 g, 3.35 mmol) in DCM (20 mL) at 0° C. The reaction mixture was stirred at room temperature for 16 h. A solution containing a mixture of NaHCO3 and Na2S2O3 was added and the resulting mixture was stirred for 30 min. The mixture was then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography eluting with 40% EtOAc in hexanes to give the sub-title compound as a colorless oil (1.15 g, 95%). LCMS calc. for C19H26N2NaO5 (M+Na)+ m/z=385.2. found 385.0.

Workup

  1. additionA solution containing
  2. additionwas added
  3. stirringthe resulting mixture was stirred for 30 min
  4. extractionThe mixture was then extracted with DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography
  8. washeluting with 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-af3d32e3eed94e57934c9b7982fe507b
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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