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

HRID 557834ノート

反応式

HRID 557834 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, water and 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, water and brine successively
  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-6a667d722ac2449aaac09aac5d4c5c97
出典データセット
uspto-grants-2011_11
特許番号
US08058288B2

反応ノート

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