3,4-dihydro-2H-pyran → (2R)-1-morpholino-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

HRID 1654203

反応式

HRID 1654203 の反応式
[OH:1][C@H:2]([CH3:11])[C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][C@H:2]([CH3:11])[C:3]([N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)=[O:4]

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 14978393(R)-2-Hydroxy-1-morpholinopropan-1-one

生成物 1

HCID 10977653(2R)-1-morpholino-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one収率 85.4%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 6344Dichloromethane溶媒

実験手順

To a dichloromethane (500 ml) solution of N-[(2R)-2-hydroxypropionyl]morpholine (141 g) was added p-toluenesulfonic acid mono hydrate (1.67 g). To the mixture was added dropwise (30 minutes) 3,4-dihydro-2H-pyran (89.3 g) under ice-cooling, which was stirred for 30 minutes at room temperature. The reaction mixture was washed with a 5% aqueous solution of sodium hydrogen carbonate (150 ml×2), which was dried (magnesium sulfate), then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel chromatography [silica gel 800 g, eluent: hexane-ethyl acetate=8:1→ethyl acetate] to give N-[(2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine (184 g) as a pale yellow oily product.

後処理

  1. temperaturecooling
  2. washThe reaction mixture was washed with a 5% aqueous solution of sodium hydrogen carbonate (150 ml×2), which
  3. dry with materialwas dried (magnesium sulfate)
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by means of a silica gel chromatography [silica gel 800 g, eluent: hexane-ethyl acetate=8:1→ethyl acetate]

出典と根拠

ORDレコード
ord-6a308ecf26c34b0ba4ca531c4f7d66e7
出典データセット
uspto-grants-1995_04
特許番号
US05405861

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