Water → 6-(4-Morpholinyl)-2-pyridinemethanol

HRID 2183507ノート

反応式

HRID 2183507 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[N:33]=[C:32]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:31]=[CH:30][CH:29]=1)(C(C)(C)C)(C)C.O>C1COCC1>[N:34]1([C:32]2[N:33]=[C:28]([CH2:27][OH:26])[CH:29]=[CH:30][CH:31]=2)[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1

参加物

5

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 224731974-[6-(Tert-butyldimethylsilanyloxymethyl)-pyridin-2-yl]morpholine

生成物 1

HCID 224732166-(4-Morpholinyl)-2-pyridinemethanol収率 82.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of tetrabutylammonium fluoride (1.44 mmol) in THF (1.0 M, 1.44 ml) was added to a stirred solution of 4-[6-(tert-butyldimethylsilanyloxymethyl)-pyridin-2-yl]morpholine (370 mg, 1.2 mmol) in THF (10 ml) at room temperature under N2 and the reaction mixture was stirred at room temperature for 1 h. H2O (30 ml) was added and the organic were extracted with EtOAc (150 ml), then washed with brine (50 ml), dried and concentrated under reduced. The mixture was purified by column chromatography on silica using 100% Et2O as eluent to yield the desired hydroxymethylpyridine (192 mg, 82%). 1H NMR (360 MHz, CDCl3) δ 7.49 (1H, dd, J=8.4, 7.4 Hz), 6.57 (1H, d, J=7.4 Hz), 6.51 (1H, d, J=8.4 Hz), 4.62 (2H, s), 3.83 (4H, t, J=4.9 Hz), 3.50 (4H, t, J=4.9 Hz).

後処理

  1. extractionthe organic were extracted with EtOAc (150 ml)
  2. washwashed with brine (50 ml)
  3. customdried
  4. concentrationconcentrated
  5. customThe mixture was purified by column chromatography on silica using 100% Et2O as eluent

出典と根拠

ORDレコード
ord-7dbea7aeb97049f29426dc30322ce781
出典データセット
uspto-grants-2005_05
特許番号
US06900209B2

反応ノート

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