Diisopropylethylamine → 1'-(1-[4-(2-Phenylethoxy)phenyl]cyclopropylcarbonyl)-3H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one

HRID 504290ノート

反応式

HRID 504290 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2N=N1.Cl.Cl.[NH:43]1[CH2:47][CH2:46][C:45]2([C:55]3[CH:54]=[CH:53][N:52]=[CH:51][C:50]=3[C:49](=[O:56])[O:48]2)[CH2:44]1.[CH:57](N(CC)C(C)C)(C)[CH3:58]>CN(C)C=O>[C:24]1([CH2:57][CH2:58][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3([C:11]([N:43]4[CH2:47][CH2:46][C:45]5([C:55]6[CH:54]=[CH:53][N:52]=[CH:51][C:50]=6[C:49](=[O:56])[O:48]5)[CH2:44]4)=[O:13])[CH2:9][CH2:10]3)=[CH:6][CH:7]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 225049291-(4-Hydroxyphenyl)cyclopropane-1-carboxylic acidHCID 666621753H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one dihydrochloride

生成物 1

HCID 666619571'-(1-[4-(2-Phenylethoxy)phenyl]cyclopropylcarbonyl)-3H-spiro[furo[3,4-c]pyridine-1,3'-pyrrolidin]-3-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1-(4-Hydroxyphenyl)cyclopropane-carboxylic acid (0.19 g, 1.0 mmol), benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (0.24 g, 1.0 mmol) and N,N-dimethylformamide (1.5 ml) were mixed with stirring at room temperature for ten minutes. To the mixture, with stirring, was added 3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one dihydrochloride (0.47 g, 1.0 mmol), followed by N,N-Diisopropylethylamine (0.55 ml, 3.2 mmol). The resulting mixture was stirred at r.t. overnight. Then the reaction was quenched with water, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated KH2PO4 solution (×2), water (×1), saturated NaHCO3 solution (×2), water (×1) and brine (×1) successively; then dried over Na2SO4; and then filtered. The filtrate was concentrated. The residue was further dried under high vacuum, and the desired product was obtained (0.43 g).

後処理

  1. stirringTo the mixture, with stirring
  2. stirringThe resulting mixture was stirred at r.t. overnight
  3. customThen the reaction was quenched with water
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated KH2PO4 solution (×2), water (×1), saturated NaHCO3 solution (×2), water (×1) and brine (×1) successively
  6. dry with materialthen dried over Na2SO4
  7. filtrationand then filtered
  8. concentrationThe filtrate was concentrated
  9. customThe residue was further dried under high vacuum

出典と根拠

ORDレコード
ord-82cc586544a34fbba1153e9e095c43bb
出典データセット
uspto-grants-2010_08
特許番号
US07776874B2

反応ノート

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