Potassium Carbonate → HCID 57723960, compound

HRID 1987679Notes

Reaction equation

HRID 1987679 reaction equation
C[C:2]1([CH3:12])[O:7][C@H:6]2[CH:8]=CC[O:11][C@H:5]2CO1.[C:13]([O-:16])([O-])=O.[K+].[K+].CS(N)(=O)=O.CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:45]C)C=C4)N(CC2)C1.[O-]S([O-])=O.[Na+].[Na+].O.[C:89]([OH:93])([CH3:92])([CH3:91])C>O=[Os](=O)(=O)=O>[CH3:92][C:89]1([CH3:91])[O:93][C@H:8]2[C@H:13]([OH:16])[C@H:12]([OH:45])[CH2:2][O:7][C@H:6]2[CH2:5][O:11]1

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 57723925HCID 57723925, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 57723960HCID 57723960, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of racemic cis-2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (100 mg. 0.58 mmol) in 4 mL of H2O-tert-BuOH (1:1), were added sequentially K3Fe(CN)6 (580 mg, 1.76 mmol), K2CO3 (243 mg, 1.76 mmol), MeSO2NH2 (110 mg, 1.16 mmol) and (DHQD)2PHAL (60 mg, 0.08 mmol) at 0° C. The solution was stirred for 5 min and OsO4 (10 μL, 25 wt % in tert-BuOH) was added and stirring was maintained for 62 H at ambient temperature. Na2SO3 (100 mg) was added and the mixture was stirred for 30 min, filtered through filter paper and extracted with EtOAc—H2O (4:1 v/v, 100 mL×2). The combined organic layer was washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography with 100% EtOAc.

Workup

  1. stirringstirring
  2. stirringthe mixture was stirred for 30 min
  3. filtrationfiltered
  4. filtrationthrough filter paper
  5. extractionextracted with EtOAc—H2O (4:1 v/v, 100 mL×2)
  6. washThe combined organic layer was washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography with 100% EtOAc

Sources & evidence

ORD record
ord-de82430b608244d19a31b817c538e02b
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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