Sodium Sulfite → HCID 57889688, compound

HRID 1016164Notes

Reaction equation

HRID 1016164 reaction equation
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:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.[Cl:64][C:65]1[CH:70]=[CH:69][C:68]([C:71]2[C:76]([CH3:78])([CH3:77])[CH2:75][N:74]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[CH2:73][CH:72]=2)=[CH:67][CH:66]=1.S([O-])([O-])=O.[Na+].[Na+].C(O)(C)(C)C.[OH2:97]>>[Cl:64][C:65]1[CH:70]=[CH:69][C:68]([C@:71]2([OH:22])[C@@H:72]([OH:97])[CH2:73][N:74]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[CH2:75][C:76]2([CH3:77])[CH3:78])=[CH:67][CH:66]=1

Participants

6

Reactant 5

HCID 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 57889345HCID 57889345, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 57889688HCID 57889688, compoundYield 35.5%

Conditions

Temperature
0 °C

Procedure

The title compound was prepared via the method of Sharpless, et. al., J. Org. Chem. 57, 1992, 2768. A stirring suspension of AD-MIX-alpha (2.3 g, 1.554 mmol) and methanesulfonamide (148 mg, 1.554 mmol) in 1:1 tert-butanol/water (16 mL) was cooled to 0° C., then treated with tert-butyl 4-(4-chlorophenyl)-5,5-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate (500 mg, 1.554 mmol). The mixture was allowed to come to room temperature, and stirred for 8 days. The reaction was treated with sodium sulfite (3 g), stirred for 30 minutes, then extracted 3× with ethyl acetate. The combined organic phases were washed 3× with 1M NaOH, once with water, and once with brine, dried over sodium sulfate, and concentrated in-vacuo. The residue was purified over silica gel, eluting with ethyl acetate/hexanes (10%-20%-50% EtOAc) to yield the title compound (196 mg, 0.551 mmol, 35.5% yield) as a colorless foam. MS (ESI+)=378.26, (M+Na)+.

Workup

  1. customThe title compound was prepared via the method of Sharpless, et. al., J
  2. customto come to room temperature
  3. stirringstirred for 30 minutes
  4. extractionextracted 3× with ethyl acetate
  5. washThe combined organic phases were washed 3× with 1M NaOH
  6. dry with materialonce with water, and once with brine, dried over sodium sulfate
  7. concentrationconcentrated in-vacuo
  8. customThe residue was purified over silica gel
  9. washeluting with ethyl acetate/hexanes (10%-20%-50% EtOAc)

Sources & evidence

ORD record
ord-c47ab6f05f3d4b288a56e0f63f773db1
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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