Sodium borohydride → HCID 58292546, 화합물

HRID 1798101노트

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HRID 1798101 반응식
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([B:14]2[O:18]C(C)(C)C(C)(C)[O:15]2)=[CH:12][C:11]([O:23][CH3:24])=[CH:10][C:9]=1[CH3:25])=O.[BH4-].[Na+].C(OB(O)O)C1C=CC=CC=1>CO>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH:6]1[O:18][B:14]([OH:15])[C:13]2[CH:12]=[C:11]([O:23][CH3:24])[CH:10]=[C:9]([CH3:25])[C:8]1=2

참가 물질

5

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HCID 4311764Sodium borohydrideHCID 17843933Benzyl dihydrogen borateHCID 58292569HCID 58292569, 화합물

생성물 1

HCID 58292546HCID 58292546, 화합물수율 69.6%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of 4-[4-methoxy-2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-4-oxo-butyric acid methyl ester (0.33 g, 0.87 mmol) in MeOH (3 mL) was added NaBH4 (0.073 g, 1.92 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes, quenched with 6 N HCl and extracted with EtOAc. The organic extracts were dried and concentrated in vacuo. The residue was dissolved in CH3CN and treated with polymer-bounded benzyl boric acid (2 equiv) for 2 hours. The mixture was filtered, concentrated and purified by silica gel flash column chromatography to give 3-(1-hydroxy-6-methoxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-propionic acid methyl ester (0.160 g, 69%). 1H NMR (400 MHz, MeOD-d4) δ 6.98 (s, 1H), 6.80 (s, 1H), 5.25 (m, 1H), 3.80 (s, 3H), 3.60 (s, 3H), 2.50-2.30 (m, 6H), 1.77 (m, 1H).

후처리

  1. customquenched with 6 N HCl
  2. extractionextracted with EtOAc
  3. customThe organic extracts were dried
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in CH3CN
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated
  8. custompurified by silica gel flash column chromatography

출처 및 근거

ORD 기록
ord-12bfadfe50c943edb9c57a205c81f5c6
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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