1-Butanol → HCID 90123177, compound

HRID 535311Notes

Reaction equation

HRID 535311 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(O)CCC.[I:64][C:65]1[CH:70]=[CH:69][C:68]([C:71]([C:73]2[CH:78]=[CH:77][C:76]([O:79][CH3:80])=[CH:75][CH:74]=2)=[CH2:72])=[CH:67][CH:66]=1.[OH2:81]>>[I:64][C:65]1[CH:66]=[CH:67][C:68]([C:71]([C:73]2[CH:74]=[CH:75][C:76]([O:79][CH3:80])=[CH:77][CH:78]=2)([OH:22])[CH2:72][OH:81])=[CH:69][CH:70]=1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 962WaterHCID 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 86718436HCID 86718436, compound

Product 1

HCID 90123177HCID 90123177, compound

Conditions

Temperature
45 °C

Procedure

Example 44.1 was obtained by dihydroxylation: the AD-mix-alpha (1.008 g, 0.720 mmol) in tert. BuOH (20 ml)/Water (20.00 ml) was immersed in an ice-bath. After 5 minutes 1-iodo-4-(1-(4-methoxyphenyl)vinyl)benzene (example 44.2) (0.22 g, 0.654 mmol) was added as solid. The reaction mixture was heated at 45° C. overnight. The organic solvent was removed under reduced pressure and the remaining aqueous phase was extracted three times with dichloromethane. The organic phases were pooled, dried over sodium sulfate, filtered and concentrated in vacuo to obtain the title compound as slightly yellow solid.

Workup

  1. customExample 44.1 was obtained by dihydroxylation
  2. customThe organic solvent was removed under reduced pressure
  3. extractionthe remaining aqueous phase was extracted three times with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e9126c27a8142aba76af9db739a0cae
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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