Dimethyl Sulfoxide → Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate

HRID 2368101ノート

反応式

HRID 2368101 の反応式
[OH:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.CS(C)=O>O>[O:1]=[CH:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 679Dimethyl Sulfoxide2 回HCID 8471TriethylamineHCID 57517495Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

生成物 1

HCID 57517496Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate収率 68.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate (6.33 g), triethylamine (15.9 mL) and dimethyl sulfoxide (30 mL) were added dropwise a mixture of sulfur trioxide pyridine complex (10.8 g) and dimethyl sulfoxide (30 mL) at room temperature, and the obtained mixture was stirred at room temperature for 1 hr. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with 1M hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.28 g).

後処理

  1. additionwere added dropwise
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe extract was washed with 1M hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-80f163d2f83b40fda80472bb07487570
出典データセット
uspto-grants-2014_04
特許番号
US08703758B2

反応ノート

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