tert-Butanol → 3-(5-Fluoro-2-nitrophenoxy)cyclopentane-1,2-diol

HRID 406045Notes

Reaction equation

HRID 406045 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=3[CH:14]=[C:15]([O:22]C)C=C4)N(CC2)C1.[C:59]([OH:63])([CH3:62])([CH3:61])C.C1(O[C:70]2[CH:75]=[C:74]([F:76])[CH:73]=[CH:72][C:71]=2[N+:77]([O-:79])=[O:78])CCC=C1.S(S([O-])=O)([O-])(=O)=[O:81].[Na+].[Na+]>O>[F:76][C:74]1[CH:73]=[CH:72][C:71]([N+:77]([O-:79])=[O:78])=[C:70]([CH:75]=1)[O:63][CH:59]1[CH2:61][CH2:14][CH:15]([OH:22])[CH:62]1[OH:81]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 656671Sodium PyrosulfiteHCID 19702686HCID 19702686, 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 584214883-(5-Fluoro-2-nitrophenoxy)cyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

AD-mix-alpha (7.57 g) was added to t-butanol (20.0 ml) and water (25.0 ml) and stirred for 10 min. The mixture was cooled to 0° C. and 2-(cyclopent-2-enyloxy)-4-fluoro-1-nitrobenzene (1.21 g) was added. After stirring at room temperature overnight the mixture was recooled at 0° C. and sodium metabisulfite (8.13 g) was added. After 10 min the reaction mixture was stirred at room temperature for 1 h and extracted with EtOAc. The combined organic extracts were washed with brine passed through a hydrophobic frit and concentrated in vacuo to yield the desired product.

Workup

  1. stirringAfter stirring at room temperature overnight the mixture
  2. customwas recooled at 0° C.
  3. stirringAfter 10 min the reaction mixture was stirred at room temperature for 1 h
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4192d23ba5346b48e24199f2341dce5
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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