Buspirone → 6-Hydroxybuspirone

HRID 2119338

反応式

HRID 2119338 の反応式
[CH:1]1[CH:2]=[N:3][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:27](=[O:28])[CH2:26][C:21]4([CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:20][C:18]3=[O:19])[CH2:9][CH2:8]2)=[N:5][CH:6]=1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:36])C=CC=CC=1.C(Cl)Cl.CO.[NH4+].[OH-]>C1COCC1.C1(C)C=CC=CC=1>[CH:1]1[CH:6]=[N:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:27](=[O:28])[CH:26]([OH:36])[C:21]4([CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:20][C:18]3=[O:19])[CH2:9][CH2:8]2)=[N:3][CH:2]=1

参加物

6

反応物 3

HCID 2477BuspironeHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridine2 回HCID 21896990Dichloromethane methanol ammonium hydroxide

生成物 1

HCID 99309136-Hydroxybuspirone

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Buspirone (19.3 g, 50 mmole) was dissolved in dry THF (400 mL) and the resulting solution was cooled to −78° C. A solution of KN(SiMe3)2 in toluene (100 mL, 1 M) was added slowly. After the reaction mixture was stirred at −78° C. for 1 h, a solution of 2-(phenylsulfonyl)-3-phenyloxaziridine (Davis reagent, prepared according to literature method: F. A. Davis, et al., Org. Synth., 1988, 66, 203) (17.0 g, 65 mmole) in dry THF (150 mL, precooled to −78° C.) was added quickly via a cannular. After stirred for 30 mins at −78° C., the reaction was quenched with 1 N HCl solution (500 mL). It was extracted with EtOAc (3×500 mL). The aqueous layer was separated, neutralized with saturated sodium bicarbonate solution, and extracted with EtOAc (3×500 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a white solid residue which was subjected to column chromatography using CH2Cl2/MeOH/NH4OH (200:10:1) as the eluent to give pure 6-hydroxy-buspirone (I, 7.2 g) and a mixture of buspirone and 6-hydroxy-buspirone (I). The mixture was purified by above column chromatography to afford another 3.3 g of pure 6-hydroxy-buspirone (I).

後処理

  1. stirringAfter stirred for 30 mins at −78° C.
  2. customthe reaction was quenched with 1 N HCl solution (500 mL)
  3. extractionIt was extracted with EtOAc (3×500 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted with EtOAc (3×500 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a white solid residue which

出典と根拠

ORDレコード
ord-4cb48151efe546ab820dafb929e7bec8
出典データセット
uspto-grants-2004_02
特許番号
US06686361B2

関連ノート

読み込み中…