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

HRID 969096ノート

反応式

HRID 969096 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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, waterand brine successively; then dried over Na2SO4; and then filtered. The filtrate was concentrated to afford the desired product (275 mg).

後処理

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

出典と根拠

ORDレコード
ord-7045ffdf11b149b5b74eae7adebb39dc
出典データセット
uspto-grants-2007_12
特許番号
US07304081B2

反応ノート

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