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

HRID 2306861노트

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HRID 2306861 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

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, 0.5H), 2.62-2.80 (m, 1H), 2.32-2.5 (m, 0.5H), 1.72-2.32 (m, 5H).

후처리

  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

출처 및 근거

ORD 기록
ord-934764e74e054cf7b002689cc001c556
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828442B2

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