Sodium Sulfate → [2-(Morpholin-4-yl)-1,3-thiazol-4-yl]methanol

HRID 625098ノート

反応式

HRID 625098 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][CH:9]=[C:10]([C:12](OC)=[O:13])[N:11]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][OH:13])[N:11]=2)[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86700889Methyl 2-morpholinothiazole-4-carboxylate

生成物 1

HCID 10608093[2-(Morpholin-4-yl)-1,3-thiazol-4-yl]methanol収率 68.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of methyl 2-morpholinothiazole-4-carboxylate (0.76 g, 3.33 mmol) in ethyl ether (20 mL) was treated portion wise over 10 min. with lithium aluminum hydride (0.38 g, 10.01 mmol). The mixture was stirred at −78° C. for 4 hours, then slowly treated with ethyl acetate (10 mL) and sat. Na2SO4 (20 mL). The mixture was allowed to warm up to RT, diluted with ethyl acetate, washed with sat. NaHCO3 (1×), brine (1×), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on silica gel chromatography (3×10 cm, 25% AcOEt/CH2Cl2 to 100% AcOEt) to give the title material as a beige solid (0.458 g) which was then distilled (bulb to bulb, 135-145° C./0.2 torr) and afforded the desired product (0.455 g, 68%) as a white solid. LC (Method F): 0.873 min. HRMS (ESI) calcd for C8H13N2O2S [M+H]+ m/z 201.07, found 201.2. 1H NMR (CDCl3, 400 MHz) δ ppm: 6.43 (s, 1H) 4.53 (d, J=3.9 Hz, 2H) 3.79 (m, 4H) 3.44 (m, 4H) 2.17 (s, 1H).

後処理

  1. temperatureto warm up to RT
  2. washwashed with sat. NaHCO3 (1×), brine (1×)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel chromatography (3×10 cm, 25% AcOEt/CH2Cl2 to 100% AcOEt)

出典と根拠

ORDレコード
ord-4e520147885645179e1655baf731af75
出典データセット
uspto-grants-2016_04
特許番号
US09303065B2

反応ノート

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