tert-Butanol → (S)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

HRID 514001Notes

Reaction equation

HRID 514001 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.[Cl:59][C:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:63]=[C:62](C)[C:61]=1C=C.S([O-])([O-])=O.[Na+].[Na+].[C:79]([OH:83])(C)([CH3:81])[CH3:80]>ClCCl.O>[Cl:59][C:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:63]=[C:62]([CH3:61])[C:80]=1[C@H:79]([OH:83])[CH2:81][OH:22]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 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)phthalazineHCID 671260761-Chloro-3-methyl-2-vinylnaphthalene

Product 1

HCID 67127139(S)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A biphasic mixture of AD-mix-α (6.907 g) in tert-butanol (24.5 mL)/H2O (24.5 mL) was cooled to 0° C. and 1-chloro-3-methyl-2-vinylnaphthalene (4D) (1.00 g, 4.93 mmol) was added. The reaction mixture was stirred for 8 h at 0° C. Sodium sulfite (7.4 g) was added at 0° C. and the reaction was stirred for 40 minutes to give a white mixture. The mixture was diluted with dichloromethane and H2O. The mixture was extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give 4E as a white solid (0.920 g).

Workup

  1. stirringthe reaction was stirred for 40 minutes
  2. customto give a white mixture
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. dry with materialthe combined organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-665a6e6d5e65426a888ecdcb8f824c2e
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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