tert-Butanol → HCID 86684754, compound

HRID 1408887Notes

Reaction equation

HRID 1408887 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]([F: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[F:69]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 86684751HCID 86684751, compound

Product 1

HCID 86684754HCID 86684754, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

AD-mix-beta (45 g) was added portion wise to a solution of 2 (4.5 g, 26.2 mmol) in t-butanol (135 mL) and H2O (135 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. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were 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 5.0 g (92%) of 3 as a colorless oil. 1HNMR (CDCl3) δ 2.04 (2 H, brs), 2.81 (2 H, m), 3.54 (1 H, t, J=5.0 Hz), 3.75 (1 H d, J=11.0 Hz), 3.94 (1 H, m), 7.46 (1 H, d, J=9.0 Hz), 8.10 (1 H, s); LC/MS (M+1) 207.

Workup

  1. temperaturecooled to 5° C.
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed on silica gel
  7. washeluted with 67% ethyl acetate in hexanes and ethyl acetate

Sources & evidence

ORD record
ord-21dd71e274ea4335892c4a9387b81367
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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