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

HRID 855952Notes

Reaction equation

HRID 855952 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6bcd09bd6909474489ae68e6de8a107b
Source dataset
uspto-grants-2007_08
Patent number
US07262307B2

Reaction notes

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