Borane;tetrahydrofuran → Methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoate

HRID 2071055노트

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HRID 2071055 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:13]=1)[C:8](O)=[O:9])=[O:4].B.C1COCC1.C(O)(=O)C.O>C1COCC1>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([CH:13]=[C:12]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4]

참가 물질

5

반응물 3

HCID 2723981Borane;tetrahydrofuranHCID 111503713-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acidHCID 21899381Acetic acid--water (1/1)

생성물 1

HCID 57815142Methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoate수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

To a stirring solution of 234 mg of 3-(methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid in 10 mL of THF at r.t. was added 1.2 mL of BH3.THF (1.0 M in THF). After the solution was stirred at 75° C. for 3 h, 3 mL of acetic acid:H2O (1:1) was added and stirring was continued until bubbling ceased. Saturated NaHCO3 solution was added to a pH=7, and the solution was concentrated. Water was added, and the aqueous layer was extracted with EtOAc (2×). The combined extracts were washed with water and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1.5% MeOH/CHCl3) provided 191 mg of methyl 3-(hydroxymethyl)-5-(N-methylmethylsulfonamido)benzoate as a pale yellow oil in 86% yield.

후처리

  1. stirringstirring
  2. customuntil bubbling
  3. additionSaturated NaHCO3 solution was added to a pH=7
  4. concentrationthe solution was concentrated
  5. additionWater was added
  6. extractionthe aqueous layer was extracted with EtOAc (2×)
  7. washThe combined extracts were washed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash silica gel chromatography (1.5% MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-874fb8c048114fd48054e3d11314351f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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