Triphenylphosphine → (R)-(1'-benzyl-2-oxo-[1,3']bipyrrolidinyl-3-yl)-triphenyl-phosphonium bromide

HRID 855952ノート

反応式

HRID 855952 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:17][CH2:16][C@@H:15]([Br:18])[C:14]2=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]1[CH:25]=[CH:24][C:23]([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[Br-:18].[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:17][CH2:16][C@@H:15]([P+:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:23]3[CH:22]=[CH:21][CH:20]=[CH:25][CH:24]=3)[C:14]2=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 11776TriphenylphosphineHCID 23529702(R)-(1'-benzyl-3-bromo-[1,3']bipyrrolidinyl-2-one)

生成物 1

HCID 23529700(R)-(1'-benzyl-2-oxo-[1,3']bipyrrolidinyl-3-yl)-triphenyl-phosphonium bromide収率 78%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A suspension of 800 mg of 1′-benzyl-3-bromo-[1,3′]bipyrrolidinyl-2-one in 1.0 ml toluene was treated with 1.95 g of Ph3P and stirred at 110° C. for 30 min whereupon TLC indicated the reaction was complete. The brown two phase mixture was diluted with 10 ml EtOAc and the organic phase was extracted with three portions of 10 ml of saturated NaBr solution. The combined aqueous phases were washed three times with 10 ml EtOAc (to remove Ph3P), and then extracted seven times with 15 ml CH2Cl2, the combined organic phases dried over MgSO4 and concentrated to give 1.13 g (78%) of (R)-(1′-benzyl-2-oxo-[1,3′]bipyrrolidinyl-3-yl)-triphenyl-phosphonium bromide as a light brown foam. 1H-NMR (250 MHz; CDCl3, ˜1:1 mixture of diastereomers): 7.32-8.04 (m, 5H), 7.50-7.82 (m, 10H), 7.19-7.40 (m, 5H), 6.44-6.64 (m, 1H), 4.39-4.50 (m, 1H), 3.10-3.88 (m, 5H), 2.85-3.00 (m, 0.5 H), 2.62-2.80 (m, 1H), 2.32-2.5 (m, 0.5 H), 1.72-2.32 (m, 5H).

後処理

  1. extractionthe organic phase was extracted with three portions of 10 ml of saturated NaBr solution
  2. washThe combined aqueous phases were washed three times with 10 ml EtOAc (to remove Ph3P)
  3. extractionextracted seven times with 15 ml CH2Cl2
  4. dry with materialthe combined organic phases dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6bcd09bd6909474489ae68e6de8a107b
出典データセット
uspto-grants-2007_08
特許番号
US07262307B2

反応ノート

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