Triacetoxyperiodinane → 4-(2-Oxazolo[4,5-c]pyridin-2-yl-2-oxo-ethyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 217184Notes

Reaction equation

HRID 217184 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([CH2:36][CH:37]([OH:47])[C:38]2[O:39][C:40]3[CH:45]=[CH:44][N:43]=[CH:42][C:41]=3[N:46]=2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[CH2:31][CH2:32][CH:33]([CH2:36][C:37]([C:38]2[O:39][C:40]3[CH:45]=[CH:44][N:43]=[CH:42][C:41]=3[N:46]=2)=[O:47])[CH2:34][CH2:35]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 576595694-(2-Hydroxy-2-oxazolo[4,5-c]pyridin-2-ylethyl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 576595174-(2-Oxazolo[4,5-c]pyridin-2-yl-2-oxo-ethyl)piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The Dess-Martin periodinane (23.7 mg, 60 μmol) was added to a stirred solution of 4-(2-hydroxy-2-oxazolo[4,5-c]pyridin-2-yl-ethyl)piperidine-1-carboxylic acid tert-butyl ester (Preparation 7, 19.4 mg, 60 μmol) in anhydrous CH2Cl2 (2 mL). After 16 h, the reaction mixture was diluted with CH2Cl2 (15 mL), before being washed with a saturated aqueous Na2S2O3-saturated aqueous NaHCO3 solution (7:1, 3×5 mL). The CH2Cl2 layer was dried (MgSO4), filtered, and concentrated. Flash chromatography (IH-EtOAc, 1:9) provided the title compound: RT=3.39 min; m/z (ES+)=346.1 [M+H]+.

Workup

  1. washbefore being washed with a saturated aqueous Na2S2O3-saturated aqueous NaHCO3 solution (7:1, 3×5 mL)
  2. dry with materialThe CH2Cl2 layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f14b5c6ec0cb4d3aab593e329d509beb
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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