Tetrahydrofuran → Benzyl 4-{3,3,3-trifluoro-2-[(methylsulfonyl)oxy]propoxy}piperidine-1-carboxylate

HRID 2368103ノート

反応式

HRID 2368103 の反応式
[F:1][C:2]([F:24])([F:23])[CH:3]([OH:22])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].C(N(CC)CC)C.C1COCC1>O>[F:24][C:2]([F:1])([F:23])[CH:3]([O:22][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:4][O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:10][CH2:11]1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67447074Benzyl 4-(3,3,3-trifluoro-2-hydroxypropoxy)piperidine-1-carboxylate

生成物 1

HCID 86658699Benzyl 4-{3,3,3-trifluoro-2-[(methylsulfonyl)oxy]propoxy}piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A mixture of benzyl 4-(3,3,3-trifluoro-2-hydroxypropoxy)piperidine-1-carboxylate (983 mg), mesyl chloride (0.438 mL), triethylamine (0.789 mL) and THF (10 mL) was stirred at 0° C. for 1 hr, and then at room temperature overnight. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with 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 (1.12 g).

後処理

  1. customat room temperature
  2. customovernight
  3. extractionthe obtained mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-645bdbfeb14843f8810bf00ef15d3efb
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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