Tetraethylammonium tetrahydroborate → Methyl 2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylate

HRID 1909128노트

반응식

HRID 1909128 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:10]([C:18]([CH3:20])=[CH2:19])[N:9]=2)=[CH:4][CH:3]=1.[BH4-].C([N+](CC)(CC)CC)C.C([O-])(O)=[O:32].[Na+]>CO.COCCOC.O>[OH:32][C:18]([C:10]1[CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=1)([CH3:20])[CH3:19]

참가 물질

7

반응물 3

HCID 28251Tetraethylammonium tetrahydroborateHCID 516892Sodium BicarbonateHCID 67339741Methyl 2-(4-methylphenyl)-6-(prop-1-en-2-yl)pyridine-4-carboxylate

생성물 1

HCID 67339432Methyl 2-(2-hydroxypropan-2-yl)-6-(4-methylphenyl)pyridine-4-carboxylate

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of methyl 2-(4-methylphenyl)-6-(prop-1-en-2-yl)pyridine-4-carboxylate (191 mg, 0.71 mmol) in methanol (3.6 mL) and DME (3.6 mL) was added cobalt(II)mesotetraphenylporphine (2.4 mg, 3.6 mop. After 30 min, tetraethylammonium borohydride (170 mg, 1.17 mmol) was added in 3 portions over 1 h. Saturated aqueous NaHCO3 was added. The mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 90% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (165 mg). MS 286.1 (M+1).

후처리

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse phase chromatography (C-18, 90% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-3240b01d78964a7f9c81768f8054afd4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598209B2

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