Potassium Carbonate → HCID 57723935, compound

https://huagongshe.com/reaction/1987683

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Sodium Sulfite	HCID 24437	—
Reactant	Methanesulfonamide	HCID 72879	—
Reactant	1-((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)phthalazine	HCID 51003674	—
Reactant	HCID 57723925	HCID 57723925	—
Reactant	2-Methylpropan-2-ol--water (1/1)	HCID 71401949	—
Catalyst	Osmium Tetroxide	HCID 30318	—
Product	HCID 57723935	HCID 57723935	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07550607B2
Source dataset	uspto-grants-2009_06
ORD ID	ord-dcd2fee996a642129db72b61e350e3f9
Source note	uspto-grants-2009_06