Sodium Carbonate → HCID 69198981、化合物

HRID 2251895ノート

反応式

HRID 2251895 の反応式
S(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(=O)(=O)C.[NH:20]1[CH2:26][CH2:25][CH2:24][C@@H:21]1[CH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[OH:23][CH2:22][C@H:21]1[CH2:24][CH2:25][CH2:26][N:20]1[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 2724541Prolinol, (R)-HCID 22934161HCID 22934161、化合物

生成物 1

HCID 69198981HCID 69198981、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

4-Morpholinophenethyl mesylate (0.43 g, 1.51 mmol), D-prolinol (0.17 g, 1.66 mmol) and sodium carbonate (0.40 g, 2.89 mmol) were added to acetonitrile (20 ml), and they were stirred under heating at 70° C. overnight. The reaction mixture was cooled and then filtered. The filtrate was evaporated to dryness under reduced pressure, and the residue was distributed into water and ethyl acetate. The intended product was extracted from ethyl acetate layer with 1 M hydrochloric acid. The aqueous layer was neutralized and the product was again extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (R)-2-hydroxymethyl-1-(4-morpholinophenethyl)pyrrolidine in the form of a light yellow solid (0.44 g, 1.5 mmol, 100%). This product was dissolved in dichloromethane (10 ml). Triethylamine (0.29 ml, 2.1 mmol) and methanesulfonyl chloride (0.15 ml, 1.9 mmol) were added to the obtained solution at 0° C., and they were stirred at room temperature for 1 hour. The reaction mixture was distributed into 5% aqueous sodium hydrogencarbonate solution and dichloromethane. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with hexane and ethyl acetate (1:1), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (R)-3-chloro-1-(morpholinophenethyl)piperidine in the form of a white solid (0.30 g, 64%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. extractionThe intended product was extracted from ethyl acetate layer with 1 M hydrochloric acid
  5. extractionthe product was again extracted with ethyl acetate
  6. customThe organic layer was dried
  7. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-e3e1598a28ed451abff968314511a2cb
出典データセット
uspto-grants-2008_01
特許番号
US07320973B2

反応ノート

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