Sodium borohydride → HCID 58292546、化合物

HRID 1798101ノート

反応式

HRID 1798101 の反応式
[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

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 17843933Benzyl dihydrogen borateHCID 58292569HCID 58292569、化合物

生成物 1

HCID 58292546HCID 58292546、化合物収率 69.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-12bfadfe50c943edb9c57a205c81f5c6
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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