Ethyl Acetate → 3-{1-[2,3-Dihydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl]-1,2,3,6-tetrahydropyridin-4-yl}-1H-indole

HRID 49255

反応式

HRID 49255 の反応式
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:18][O:17][C:16]3[CH:19]=[CH:20][C:21]4[O:25][CH:24]=[CH:23][C:22]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.[NH:26]1[CH2:31][CH:30]=[C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][CH:33]=2)[CH2:28][CH2:27]1.C(OCC)(=O)C>CS(C)=O>[O:14]1[C:15]2[C:22]3[CH:23]=[CH:24][O:25][C:21]=3[CH:20]=[CH:19][C:16]=2[O:17][CH2:18][CH:13]1[CH2:12][N:26]1[CH2:27][CH:28]=[C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][CH:33]=2)[CH2:30][CH2:31]1

参加物

5

実験手順

A solution of 0.40 g (1.1 mmole) of (2R)-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate and 1.0 g (5.0 mmole) of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole in 10 mL of DMSO was heated under nitrogen at 80° C. for 4 hours. After the reaction had cooled to room temperature, 400 mL of ethyl acetate was added and the solution was washed with 250 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on silica gel with 2% methanol in chloroform to give 0.27 g of the (S)-enantiomer of the title compound as a white solid, m.p. 208-209° C.

後処理

  1. washthe solution was washed with 250 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customchromatographed on silica gel with 2% methanol in chloroform

出典と根拠

ORDレコード
ord-276e64281b7c4ca98250d148688195c5
出典データセット
uspto-grants-2004_03
特許番号
US06706736B2

関連ノート

読み込み中…