tert-Butanol → HCID 22995909, compound

HRID 1167193Notes

Reaction equation

HRID 1167193 reaction equation
[F:1][C:2]([F:20])([F:19])[S:3]([O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=C(C=C)[CH:11]=[CH:12][CH:13]=2)[N:8]=1)(=[O:5])=[O:4].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:42]C)C=C4)N(CC2)C1.S(=O)(O)[O-].[Na+].[C:84]([OH:88])(C)([CH3:86])[CH3:85]>O>[F:1][C:2]([F:20])([F:19])[S:3]([O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:85]([CH:84]([OH:88])[CH2:86][OH:42])[CH:11]=[CH:12][CH:13]=2)[N:8]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 6386tert-Butanol2×HCID 22995915HCID 22995915, compoundHCID 23665763Sodium BisulfiteHCID 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 22995909HCID 22995909, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2-trifluoromethanesulfonyloxy-8-vinylquinoline in 37 ml of tert-butanol and 37 ml of water is added to a suspension, cooled to 0° C. with an ice bath, of AD-mix-α in 300 ml of tert-butanol and 300 ml of water. The reaction mixture is stirred at 0° C. for 16 h and then sodium bisulfite with 300 ml of water is added. The mixture is stirred for 1 h at ambient temperature and extraction is carried out with ethyl acetate (3×200 ml). The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 1/1) to provide 12.0 g of 2-trifluoromethanesulfonyloxy-8-(1,2-dihydroxyethyl)quinoline in the form of a yellow oil. (Yield: 80%)

Workup

  1. stirringThe mixture is stirred for 1 h at ambient temperature
  2. extractionextraction
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-e964d3e7acf74efdb64e056b514bd8fa
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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