1,4-Bis(dihydroquinidine)phthalazine → (2R)-2-(3-bromophenyl)-1,2-propanediol

HRID 1157731Notes

Reaction equation

HRID 1157731 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]=C)[CH:3]=1.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:25]([O:32]C)C=C4)N(CC2)C1.C([OH:73])(C)(C)C.O>>[Br:1][C:2]1[CH:3]=[C:4]([C@:8]([OH:73])([CH3:9])[CH2:25][OH:32])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 124071321-Bromo-3-(prop-2-en-1-yl)benzeneHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 10105280(2R)-2-(3-bromophenyl)-1,2-propanediol

Conditions

Temperature
4 °C

Procedure

A mixture of 1-bromo-3-(2-propenyl)benzene from step 1 (2.9 g, 15 mmol) and AD-mix-β (Aldrich, 21.0 g) in t-BuOH-H2O (1:1, 150 mL) was vigorously stirred at 4° C. for 16 h. The reaction was quenched with solid Na2SO3 (5.0 g) and diluted with ethyl acetate (150 mL). The aqueous was separated and extracted with ethyl acetate. The combine organic phase was washed with brine, dried and filtered through a short path of silica gel. Removal of the solvent gave essentially pure title compound.

Workup

  1. customThe reaction was quenched with solid Na2SO3 (5.0 g)
  2. additiondiluted with ethyl acetate (150 mL)
  3. customThe aqueous was separated
  4. extractionextracted with ethyl acetate
  5. washThe combine organic phase was washed with brine
  6. customdried
  7. filtrationfiltered through a short path of silica gel
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-086a6a894d3a430c80f8e471244168a9
Source dataset
uspto-grants-2010_10
Patent number
US07807692B2

Reaction notes

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