Diisopropylethylamine → (1R)-1'-{[1-(2-Fluoro-4-pyridin-2-ylphenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

HRID 557834Notes

Reaction equation

HRID 557834 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[C:4]([F:14])[CH:3]=1.CC1(C)[C@@H]2CC[C@@]1(CS(O)(=O)=O)C(=O)C2.[NH:30]1[CH2:34][CH2:33][C@@:32]2([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[C:36](=[O:43])[O:35]2)[CH2:31]1.F[P-](F)(F)(F)(F)F.[N:51]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:55]2C=[CH:57][CH:58]=[CH:59][C:54]=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[F:14][C:4]1[CH:3]=[C:2]([C:55]2[CH:54]=[CH:59][CH:58]=[CH:57][N:51]=2)[CH:7]=[CH:6][C:5]=1[C:8]1([C:11]([N:30]2[CH2:34][CH2:33][C@@:32]3([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[C:36](=[O:43])[O:35]3)[CH2:31]2)=[O:13])[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576855791-(4-Chloro-2-fluorophenyl)cyclopropane-1-carboxylic acidHCID 86602274[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid (1R)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Product 1

HCID 66661642(1R)-1'-{[1-(2-Fluoro-4-pyridin-2-ylphenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4-chloro-2-fluorophenyl)cyclopropanecarboxylic acid (0.15 g, 0.7 mmol), [(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid-(1R)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (1:1) salt (0.29 g, 0.7 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.34 g, 0.77 mmol), and N,N-diisopropylethylamine (0.43 ml, 2.4 mmol) in N,N-dimethylformamide (2.0 ml) was stirred at room temperature overnight. The mixture then was diluted with ethyl acetate. The resulting solution was washed with saturated NaHCO3 solution, water, 1N HCl solution, water and brine successively; then dried over Na2SO4; and then filtered. The filtrate was concentrated to afford the desired product (275 mg).

Workup

  1. washThe resulting solution was washed with saturated NaHCO3 solution, water, 1N HCl solution, water and brine successively
  2. dry with materialthen dried over Na2SO4
  3. filtrationand then filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6a667d722ac2449aaac09aac5d4c5c97
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

Loading…