Water → (3S)-2-Methyl-3-(trityl-amino)-pentan-2-ol

HRID 1984272ノート

反応式

HRID 1984272 の反応式
[C:1]([NH:20][C@@H:21]([CH2:25][CH3:26])[C:22](=[O:24])[CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Mg]I.O>CCOCC>[CH3:23][C:22]([OH:24])([C@@H:21]([NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:25][CH3:26])[CH3:27]

参加物

5

反応物 3

HCID 962WaterHCID 57714152(3S)-3-(Trityl-amino)-pentan-2-oneHCID 178418373HCID 178418373、化合物

生成物 1

HCID 57714158(3S)-2-Methyl-3-(trityl-amino)-pentan-2-ol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a stirred solution of (3S)-3-(trityl-amino)-pentan-2-one (0.59 g, 1 eq, 1.72 mmol) in Et2O (100 mL) under an argon atmosphere at room temperature, was added methylmagnesium iodide (3 M in Et2O, 1.72 mL, 3 eq, 5.16 mmol) dropwise. The solution was placed in a preheated oil bath at 45° C. and refluxed at this temperature for 16 h. The mixture was recooled to 0° C., H2O (100 mL) added, the solution filtered through Celite, and the Celite washed with more Et2O (50 mL). The combined organic phase was separated, the aqueous phase was extracted with Et2O (2×50 mL), and the combined organic phase washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by silica gel column chromatography, eluted with hexane: Et2O (100:0→90:10) to afford the title compound as a light yellow oil. Yield: 0.10 g (16%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.27 (t, J=7.10 Hz, —NHCH(CH2CH3(CH3)OH), 0.99 & 1.25 (2×s, 6H, —NHCH(CH2CH3)C(CH3)2OH), 0.75-1.42 (m, 2H, —NHCH(CH2CH3)C(CH3)2OH), 1.88 (m, 1H, —NHCH(CH2 CH3)C(CH3)2OH), 2.92 (m, 1H, —NHCH(CH2CH3)C(CH3)2OH), 4.32 (s, 1H, —NHCH (CH2CH3)C(CH3)2OH), 7.18-7.46 (m, 15H, 3×Ph).

後処理

  1. customThe solution was placed in a preheated oil bath at 45° C.
  2. temperaturerefluxed at this temperature for 16 h
  3. customwas recooled to 0° C.
  4. filtrationthe solution filtered through Celite
  5. washthe Celite washed with more Et2O (50 mL)
  6. customThe combined organic phase was separated
  7. extractionthe aqueous phase was extracted with Et2O (2×50 mL)
  8. washthe combined organic phase washed with brine (50 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customThe residue was purified by silica gel column chromatography
  12. washeluted with hexane: Et2O (100:0→90:10)

出典と根拠

ORDレコード
ord-df0ac30648ab46bc9fa603742c63cc61
出典データセット
uspto-grants-2009_06
特許番号
US07544689B2

反応ノート

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