tert-Butanol → HCID 86684756, compound

HRID 1408890Notes

Reaction equation

HRID 1408890 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.C([C:62]1[CH:63]=[C:64]([CH3:69])[C:65]([Cl:68])=[N:66][CH:67]=1)C=C.S([O-])([O-])=O.[Na+].[Na+].[C:76]([OH:80])(C)([CH3:78])[CH3:77]>O>[Cl:68][C:65]1[N:66]=[CH:67][C:62]([CH2:77][C@@H:76]([OH:80])[CH2:78][OH:22])=[CH:63][C:64]=1[CH3:69]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 86684757HCID 86684757, compound

Product 1

HCID 86684756HCID 86684756, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

AD-mix-beta (27.8 g) was added portion wise to a solution of 51 (2.7 g, 16.2 mmol) in t-butanol (83 mL) and H2O (83 mL) at 5° C. The mixture was stirred at room temperature for 16 hrs and then cooled to 5° C. and treated with excess sodium sulfite for 20 min. It was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, concentrated and chromatographed on silica gel eluted with 67% ethyl acetate in hexanes and ethyl acetate to afford 3.2 g (98%) of 52 as an oil which was confirmed by LC/MS and was used directly for the next step.

Workup

  1. temperaturecooled to 5° C.
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customchromatographed on silica gel
  8. washeluted with 67% ethyl acetate in hexanes and ethyl acetate

Sources & evidence

ORD record
ord-85fd97b94d954c63bc8c486f7680a5af
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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