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

HRID 926135ノート

反応式

HRID 926135 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b302c338847a408696d055d896cbedc4
出典データセット
uspto-grants-2016_03
特許番号
US09284323B2

反応ノート

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