Triacetoxyperiodinane → HCID 117698030, compound

HRID 1778503Notes

Reaction equation

HRID 1778503 reaction equation
[OH:1][CH2:2][C:3]12[N:10]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH:7]([CH2:8][CH2:9]1)[CH2:6][O:5][CH2:4]2.[CH3:17]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]12[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH2:8][CH2:9]1)[CH2:6][O:5][CH2:4]2)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 117697875HCID 117697875, compound

Product 1

HCID 117698030HCID 117698030, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isopropyl 5-(hydroxymethyl)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate (73 mg, 0.3 mmol) in DCM (mL) was added Dess-Martin (191 mg, 0.45 mmol) at ice-bath. The mixture was allowed to warm to room temperature while stirred for 2 h. Then the mixture was diluted with DCM (50 mL) and washed with saturated NaHCO3 (50 mL) three times and water (50 mL) three times, dried over anhydrous sodium sulfate and concentrated in vacuo to afford tert-butyl 5-formyl-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate (71 mg, 98%) which was used for next step without further purification. MS: calc'd (MH+) 242, measured (MH+) 242.

Workup

  1. washwashed with saturated NaHCO3 (50 mL) three times and water (50 mL) three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b6d174c988f400fb93bf2afe678e4ce
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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