tert-Butanol → HCID 20714290, compound

HRID 2270090Notes

Reaction equation

HRID 2270090 reaction equation
[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=C(C=C)[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].[C:16]([OH:20])(C)([CH3:18])[CH3:17].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+].[Na+]>O>[CH2:1]([C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[C:17]([C@H:16]([OH:20])[CH2:18][OH:42])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 18331356HCID 18331356, 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 20714290HCID 20714290, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2.0 g of 2-ethyl-3-methyl-8-vinylquinoline, 65 ml of t-butanol and 65 ml of water are introduced into a 250 ml round-bottomed flask. The solution is cooled to 0° C. on an ice bath and 16.8 g of AD-mix-α (complex based on K2OsO2(OH)4, Fe(CN)6 and dihydroquinidine 1,4-phthalazinediyl diether as ligand) are added. Stirring is continued for 18 h at 0° C. and a solution of 12.6 g of sodium sulphite in 30 ml of water is added. The mixture obtained is stirred for 1 h at room temperature and is then extracted with ethyl acetate (2×200 ml). The organic phase is dried over magnesium sulphate and concentrated. The residue is purified by column chromatography on silica (elution solvent: 3/7 ethyl acetate/heptane). 2.0 g (yield: 86.5%) of (+)-2-ethyl-3-methyl-8-(1(S),2-dihydroxyethyl)quinoline are obtained in the form of a white solid.

Workup

  1. customThe mixture obtained
  2. stirringis stirred for 1 h at room temperature
  3. extractionis then extracted with ethyl acetate (2×200 ml)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography on silica (elution solvent: 3/7 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-aed5e87a9e4647f7ba19a0ce324ee1a9
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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