3,3-Diphenylpyrrolidine → 1-[2-(3,3-Diphenylpyrrolidin-1-yl)-2-oxoethyl]-3,3-bis(4-fluorophenyl)pyrrolidin-2-one

HRID 1667127

反応式

HRID 1667127 の反応式
[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[CH2:29][CH2:28][N:27]([CH2:30][C:31](O)=[O:32])[C:26]2=[O:34])=[CH:21][CH:20]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:11][CH2:10][N:9]([C:31](=[O:32])[CH2:30][N:27]3[CH2:28][CH2:29][C:25]([C:22]4[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=4)([C:35]4[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=4)[C:26]3=[O:34])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 4182423,3-DiphenylpyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673571912-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

生成物 1

HCID 673594591-[2-(3,3-Diphenylpyrrolidin-1-yl)-2-oxoethyl]-3,3-bis(4-fluorophenyl)pyrrolidin-2-one

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3,3-diphenylpyrrolidine (Example 17A, 0.22 g, 1.00 mmol) in dichloromethane (25 mL) under nitrogen was added 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (Example 58D, 0.33 g, 1.00 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.39 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (0.012 g, 0.10 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with 3% methanol/dichloromethane gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.14-7.36 (m, 14H), 6.95-7.01 (m, 4H), 4.22 (s, 1H), 4.17 (s, 1H), 4.10 (s, 1H), 4.08 (s, 1H), 3.51-3.60 (m, 3H), 3.42 (t, J=6.7 Hz, 1H), 2.72-2.80 (m, 2H), 2.62 (t, J=6.6 Hz, 1H), 2.53 (t, J=6.8 Hz, 1H); MS (DCI+) m/z 537 (M+H)+.

後処理

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned in ethyl acetate/water (8:2)
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography eluting with 3% methanol/dichloromethane

出典と根拠

ORDレコード
ord-a6444c8f10e14e61ba3143d43e9c6dbf
出典データセット
uspto-grants-2011_10
特許番号
US08044069B2

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