Isopropanol → HCID 67384826, compound

HRID 1471938Notes

Reaction equation

HRID 1471938 reaction equation
[CH2:1]([C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1)CC=C.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:37]C)C=C4)N(CC2)C1.[O-]S([O-])=O.[Na+].[Na+].[CH:80]([OH:83])([CH3:82])[CH3:81]>O>[C:10]1([C:7]2[CH:6]=[C:5]([CH2:1][CH2:81][C@@H:80]([OH:83])[CH2:82][OH:37])[NH:9][N:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 24437Sodium SulfiteHCID 11615362HCID 11615362, compoundHCID 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)phthalazine

Product 1

HCID 67384826HCID 67384826, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-(but-3-enyl)-3-phenyl-1H-pyrazole (3.0 g, 15.13 mmol) in iso-propanol (20 mL) and H2O (20 mL), was added AD-mix-α (20.0 g) at room temperature. The reaction was stirred for 48 h at room temperature. The reaction was poured into saturated Na2SO3 (20 mL) and extracted with ethyl acetate. The extract was dried over MgSO4 and concentrated under reduced pressure to give the title compound (2.45 g) as an oil, which was used without further purification. LCMS m/z=232.9 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92c87af7f9ae40719f46345842a91a3a
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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