Potassium Carbonate → (S)-3-hydroxy-1-(4-pyrrolidinophenethyl)pyrrolidine

HRID 2251902ノート

反応式

HRID 2251902 の反応式
S(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(=O)(=O)C.Cl.[NH:20]1[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:25][C@H:22]1[CH2:23][CH2:24][N:20]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH2:21]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 22309122(S)-3-Hydroxypyrrolidine hydrochlorideHCID 229341624-Pyrrolidinophenethyl mesylate

生成物 1

HCID 69197702(S)-3-hydroxy-1-(4-pyrrolidinophenethyl)pyrrolidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

4-Pyrrolidinophenethyl mesylate (13.45 g, 50.0 mmol), (S)-3-pyrrolidinol hydrochloride (5.56 g, 45.0 mmol) and potassium carbonate (18.63 g, 135 mmol) were added to acetonitrile (200 ml), and they were heated at 90° C. for 3 hours. 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 the ethyl acetate layer with 1 M hydrochloric acid. The aqueous layer was neutralized and then the product was again extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (S)-3-hydroxy-1-(4-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow solid (6.30 g, 52%).

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 the 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-138df2b0b96a49639ae1365f6f7adff0
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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