Potassium Carbonate → HCID 57723935, compound

HRID 1987683Notes

Reaction equation

HRID 1987683 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 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 57723925HCID 57723925, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 57723935HCID 57723935, 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 (52 mg. 0.30 mmol) in 4 mL of H2O-tert-BuOH (1:1), were added sequentially K3Fe(CN)6 (312 mg, 0.90 mmol), K2CO3 (131 mg, 0.90 mmol), MeSO2NH2 (55 mg, 0.60 mmol) and (DHQ)2PHAL (23 mg, 0.03 mmol) at 0° C. The mixture was stirred for 5 min., OsO4 (10 μL, 25 wt % in tert-BuOH) was added and the mixture was stirred for 64 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 layers were washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography with 100% EtOAc.

Workup

  1. stirringthe mixture was stirred for 64 H at ambient temperature
  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 layers were 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-dcd2fee996a642129db72b61e350e3f9
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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