Benzcatechinborane → (S)-ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate

HRID 926135Notes

Reaction equation

HRID 926135 reaction equation
[CH3:1][C:2]1[C:3]([C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[B]1OC2C(=CC=CC=2)O1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([C@H:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:4]([O:13][S:14]([C:17]([F:19])([F:20])[F:18])(=[O:15])=[O:16])[C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 6327445BenzcatechinboraneHCID 89676862Ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

Product 1

HCID 89681708(S)-ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of ethyl 2-(3,4-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (3.93 g, 9.72 mmol) and (R)-2-methyl-CBS-oxazaoborolidine (0.539 g, 1.94 mmol) in anhydrous toluene (30 mL) at −40° C. was added dropwise a solution of catecholborane (1.40 mL, 13.22 mmol) in toluene (5 mL) over 20 minutes to give a pale yellow reaction mixture. The reaction mixture was stirred for another 20 minutes and quenched with saturated sodium carbonate solution and ethyl acetate was added. The mixture was stirred for 30 minutes, the aqueous layer removed and the organic layer washed with saturated sodium carbonate solution (3×), brine and dried (MgSO4) and filtered. Concentration and purification by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) gave the desired product. LCMS-ESI+ (m/z): [M+Na]+ calcd for C17H17F3NaO6S: 429.37. Found: 428.8.

Workup

  1. customto give a pale yellow reaction mixture
  2. customquenched with saturated sodium carbonate solution and ethyl acetate
  3. additionwas added
  4. stirringThe mixture was stirred for 30 minutes
  5. customthe aqueous layer removed
  6. washthe organic layer washed with saturated sodium carbonate solution (3×), brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationConcentration and purification by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b302c338847a408696d055d896cbedc4
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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