Water → HCID 54078618, compound

HRID 1106892Notes

Reaction equation

HRID 1106892 reaction equation
C([OH:5])(C)(C)C.O.CC[C@H]1[C@H]2C[C@H]([C@H](OC3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:34]([O:41][C@H:42]([C:53]4C=CN=[C:59]5[C:54]=4[CH:55]=[C:56]([O:63]C)[CH:57]=[CH:58]5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[CH2:34]([O:41][C:42]1[CH:53]=[C:54]([C@H:55]([OH:5])[CH2:56][OH:63])[CH:59]=[CH:58][CH:57]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 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 54078618HCID 54078618, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At 0° C. were combined t-butyl alcohol (150 mL), water (150 mL), and AD-mix-α (42 g). Example 1 (6.4 g, 30 mmol) was added and stirred for 3.5 hours. The reaction was refrigerated overnight (15.5 hours), stirred for 8 hours, refrigerated for another 16 hours, and stirred for a further 1 hour. Sodium sulphite (45 g, 36 mmol) was added and the reaction stirred for 2 hours at room temperature. The mixture was poured into ethyl acetate (300 mL) and the aqueous extracted with ethyl acetate (3×150 mL). The organics were dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (ethyl acetate:heptane 9:1) gave the product as a yellow oil, 30 mmol, 100%.

Workup

  1. customAt 0° C.
  2. waitThe reaction was refrigerated overnight
  3. stirring(15.5 hours), stirred for 8 hours
  4. waitrefrigerated for another 16 hours
  5. stirringstirred for a further 1 hour
  6. stirringthe reaction stirred for 2 hours at room temperature
  7. extractionthe aqueous extracted with ethyl acetate (3×150 mL)
  8. dry with materialThe organics were dried (MgSO4)
  9. customthe solvent removed in vacuo
  10. customPurification by column chromatography (ethyl acetate:heptane 9:1)

Sources & evidence

ORD record
ord-c4d20de471d447f9a00b32a11b5b8584
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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