Triacetoxyperiodinane → HCID 90408321, compound

HRID 1855102Notes

Reaction equation

HRID 1855102 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][CH2:25][OH:26])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][CH:25]=[O:26])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22607107sodium thiosulfate NaHCO3HCID 90408750HCID 90408750, compound

Product 1

HCID 90408321HCID 90408321, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of Example 57 compound [4-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butan-1-ol] (110 mg, 0.312 mmol) in DCM (3 mL) was added Dess-Martin periodinane (159 mg, 0.375 mmol) over 5 min. The reaction mixture was slowly warmed up to rt and stirred at rt for 2 h. Sat′d aq. NaHCO3—Na2S2O3 was then added, and the reaction mixture was stirred at rt for 5 min. The layers were separated, and the organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was chromatographed (SiO2; continuous gradient of EtOAc/hexanes from 0 to 40%) to give the title compound as a white solid. (60 mg, 55% yield and 98% purity) 1H NMR (400 MHz, CDCl3) δ 9.80 (s, 1H), 7.41-7.32 (m, 3H), 7.32-7.27 (m, J=15.8 Hz, 1H), 7.20-7.07 (m, 1H), 7.05-6.98 (m, 1H), 6.87 (ddd, J=8.1, 2.5, 1.1 Hz, 1H), 3.83 (s, 2H), 2.46 (td, J=7.3, 1.5 Hz, 2H), 2.09-1.95 (m, 5H), 1.81-1.58 (m, 7H), 1.23-1.14 (m, 2H).

Workup

  1. stirringthe reaction mixture was stirred at rt for 5 min
  2. customThe layers were separated
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed (SiO2; continuous gradient of EtOAc/hexanes from 0 to 40%)

Sources & evidence

ORD record
ord-91acc09d055343a4997759736b179f71
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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