1,4-Bis(dihydroquinidine)phthalazine → HCID 57456807, compound

HRID 1437603Notes

Reaction equation

HRID 1437603 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.[N+:59]([C:62]1[CH:76]=[CH:75][C:65]([C:66]([O:68][CH2:69][CH2:70][CH2:71]CC=C)=[O:67])=[CH:64][CH:63]=1)([O-:61])=[O:60].[C:77]([OH:81])(C)([CH3:79])[CH3:78].O>CC(=O)OCC>[N+:59]([C:62]1[CH:76]=[CH:75][C:65]([C:66]([O:68][CH2:69][CH2:70][CH2:71][CH2:78][C@@H:77]([OH:81])[CH2:79][OH:22])=[O:67])=[CH:64][CH:63]=1)([O-:61])=[O:60]

Participants

5

Reactant 3

HCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 59805529HCID 59805529, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 57456807HCID 57456807, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of AD-mix-beta (34 g) in t-BuOH—H2O (1:1, 0.077 M) at 0° C., was added hex-5-en-1-yl 4-nitrobenzoate (6 g, 24.07 mmol). The reaction was stirred at 0° C. overnight. The reaction mixture was diluted with 250 mL of EA, quenched by addition of 10 g of sodium metabisulfite and stirred 30 min at 0° C. The mixture was allowed to stir at rt for 1 h then was extracted 3 times with EtOAc, washed with brine, dried over Na2SO4, filtered and evaporated. The compound was recrystallized with ether and stirred in the cold room overnight for twice to afford 3.3 g of the titled compound as a white solid (greater than 99% in e.e. by Mosher derivatives analysis). 1H NMR (500 MHz, acetone-d6): δ 8.36 (d, 2H), 8.27 (d, 2H), 4.38 (t, 2H), 3.62-3.54 (m, 3H), 3.49-3.45 (m, 1H), 3.41-3.35 (m, 1H), 1.87-1.77 (m, 2H), 1.69-1.62 (m, 1H), 1.59-1.49 (m, 2H), 1.46-1.40 (m, 1H).

Workup

  1. customquenched by addition of 10 g of sodium metabisulfite
  2. stirringstirred 30 min at 0° C
  3. stirringto stir at rt for 1 h
  4. extractionthen was extracted 3 times with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe compound was recrystallized with ether
  10. stirringstirred in the cold room overnight for twice

Sources & evidence

ORD record
ord-cbb228a9287546b4b6159a5d5ae08479
Source dataset
uspto-grants-2009_11
Patent number
US07622502B2

Reaction notes

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