Carbon tetrabromide → 1-(2-Bromoethyl)-3,3-diphenylpyrrolidin-2-one

HRID 1667134

反応式

HRID 1667134 の反応式
O[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:21].C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:23][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:21]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 673575371-(2-Hydroxyethyl)-3,3-diphenylpyrrolidin-2-one

生成物 1

HCID 673587991-(2-Bromoethyl)-3,3-diphenylpyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of the product from Example 64A (0.3, 1.1 mmol) in methylene chloride was added carbon tetrabromide (0.7 g, 2.13 mmol) and triphenylphosphine (0.56 g, 2.13 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, and the obtained residue was chromatographed on silica gel eluting with 10-30% ethyl acetate/hexane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.31 (m, 10H), 3.78 (t, J=6.44 Hz, 2H), 3.54 (t, J=5.59 Hz, 2H), 3.49 (t, J=5.76 Hz, 2H), 2.80 (t, J=6.44 Hz, 2H); MS (ESI+) m/z 345 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained residue was chromatographed on silica gel eluting with 10-30% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-86881dcc2e0e4a86a5db31abf03f66a3
出典データセット
uspto-grants-2011_10
特許番号
US08044069B2

関連ノート

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