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

HRID 557827노트

반응식

HRID 557827 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 (x2), water (x1), saturated NaHCO3 solution (x2), water (x1) and brine (x1) 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).

후처리

  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 (x2), water (x1), saturated NaHCO3 solution (x2), water (x1) and brine (x1) 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

출처 및 근거

ORD 기록
ord-7604e5f768a14723a02304e6c621ff25
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058288B2

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