Diisopropylethylamine → (1R)-1'-({1-[4-(Pyridin-4-ylmethoxy)phenyl]cyclopropyl}-carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

HRID 557831ノート

反応式

HRID 557831 の反応式
[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.[NH:14]1[CH2:18][CH2:17][C@@:16]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20](=[O:27])[O:19]2)[CH2:15]1.[CH3:28][C:29]1(C)[C@@H]2CC[C@@:30]1([CH2:37]S(O)(=O)=O)[C:31](=O)[CH2:32]2.F[P-](F)(F)(F)(F)F.[N:50]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[N:50]1[CH:32]=[CH:31][C:30]([CH2:37][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3([C:11]([N:14]4[CH2:18][CH2:17][C@@:16]5([C:22]6[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=6[C:20](=[O:27])[O:19]5)[CH2:15]4)=[O:13])[CH2:9][CH2:10]3)=[CH:6][CH:7]=2)=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 225049291-(4-Hydroxyphenyl)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 66661855(1R)-1'-({1-[4-(Pyridin-4-ylmethoxy)phenyl]cyclopropyl}-carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1-(4-hydroxyphenyl)cyclopropanecarboxylic acid (0.20 g, 1.1 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 salt (0.47 g, 1.1 mmol), Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.55 g, 1.2 mmol), and N,N-diisopropylethylamine (0.49 ml, 2.8 mmol) in methylene chloride (3 ml) 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 1N HCl aqueous solution (x2), water and brine successively; then dried over Na2SO4; and then filtered. The filtrate was concentrated to afford the desired product (0.35 g, yield: 89%).

後処理

  1. customThen the reaction was quenched with water
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with 1N HCl aqueous solution (x2), water and brine successively
  4. dry with materialthen dried over Na2SO4
  5. filtrationand then filtered
  6. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-1e7d133630fa422d98624dfb404f66cf
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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