Triacetoxyperiodinane → HCID 86645365, compound

HRID 1959614Notes

Reaction equation

HRID 1959614 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([CH2:30][OH:31])[C:25]=1[CH2:32][O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1>C1COCC1>[Cl:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([CH:30]=[O:31])[C:25]=1[CH2:32][O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67077239HCID 67077239, compound

Product 1

HCID 86645365HCID 86645365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dess-Martin periodinane (370 mg. 0.873 mmol) was added to a stirred solution of [4-chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-methanol (150 mg. 0.582 mmol) in THF (5 mL). After stirring for 2 h at room temperature the reaction was concentrated. Sat. NaHCO3 solution (20 mL) was added and extracted three times with DCM (50 mL). The combined organic layers were dried over Na2SO4 filtered and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 255.7 [M+H+].

Workup

  1. concentrationwas concentrated
  2. additionSat. NaHCO3 solution (20 mL) was added
  3. extractionextracted three times with DCM (50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-f34771091b8047cdbc4552c352c45dfc
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

Loading…