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

HRID 969090Notes

Reaction equation

HRID 969090 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e7cfa64af0464923a9ceabd2a2f6130a
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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