Tetrabutylammonium Fluoride → (S)-4-(3-Hydroxy-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

HRID 1191375ノート

反応式

HRID 1191375 の反応式
[Si]([O:8][CH2:9][C@@H:10]([CH3:24])[CH2:11][N:12]1[C:17]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:23])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][C@@H:10]([CH3:24])[CH2:11][N:12]1[C:17]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:23]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 68909987(S)-4-[3-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-6-methyl-4H-benzo[1,4]oxazin-3-one

生成物 1

HCID 68908602(S)-4-(3-Hydroxy-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The compound (S)-4-[3-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-6-methyl-4H-benzo[1,4]oxazin-3-one (101IS60-1) (1.0 g, 2.9 mmol) was dissolved in dry THF (12 mL) and TBAF (1.2 g, 3.8 mmol) was added. The reaction was stirred at rt overnight and the solution was concentrated under reduced pressure, the remaining oil was diluted with EtOAc (60 mL) and washed with brine (3×30 mL), dried (Na2SO4) filtered and concentrated under reduced pressure. The remaining oil was purified by flash chromatography (SiO2; Heptane/EtOAc 30:70) to yield an oil which crystallized upon standing (0.69 g, 76%). 1H NMR (CDCl3) δ 6.88 (d, J=8.4 Hz, 1H), 6.83-6.78 (m, 2H), 4.59 (brs 2H), 4.22 (dd J=10.0, 14.4 Hz), 3.57-3.38 (m, 3H), 2.9 (vbrs, 1H), 2.33 (s, 3H), 2.04 (m, 1H), 1.08 (d, J=7.2 Hz); 13C NMR (CDCl3) δ 165.7, 143.4, 132.3, 124.9, 117.1, 115.9, 67.6, 63.7, 43.5, 34.2, 21.3, 15.1.

後処理

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionthe remaining oil was diluted with EtOAc (60 mL)
  3. washwashed with brine (3×30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe remaining oil was purified by flash chromatography (SiO2; Heptane/EtOAc 30:70)
  8. customto yield an oil which
  9. customcrystallized

出典と根拠

ORDレコード
ord-038af9c43708437b872809c6a2c9e09b
出典データセット
uspto-grants-2014_03
特許番号
US08680115B2

反応ノート

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