Triacetoxyperiodinane → HCID 86666506, compound

HRID 1426346Notes

Reaction equation

HRID 1426346 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([CH2:22][OH:23])[CH:21]=1)[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([CH:22]=[O:23])[CH:21]=1)[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 69672941HCID 69672941, compound

Product 1

HCID 86666506HCID 86666506, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[3-bromo-5-(hydroxymethyl)phenoxy]piperidine-1-carboxylate (0.47 g, 1.2 mmol) in DCM (20 mL) at 0° C. was added Dess-Martin periodinane (0.67 g, 1.6 mmol). After stirring for 2 hours, the reaction solution was poured into saturated NaHCO3, and extracted with DCM (3×). The combined extracts were washed with brine. The organic layer was dried over sodium sulfate, decanted and evaporated to give the desired product that was used without further purification.

Workup

  1. extractionextracted with DCM (3×)
  2. washThe combined extracts were washed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customdecanted
  5. customevaporated

Sources & evidence

ORD record
ord-6d11fe5d54fc4387a23a84a546437b50
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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