Dicyclohexylcarbodiimide → (3R,4R)-1-Benzyl-3,4-bis(diphenylphosphanyl)pyrrolidine

HRID 1604054Notes

Reaction equation

HRID 1604054 reaction equation
[CH2:1]1CCC(N=C=NC2CCCCC2)C[CH2:2]1.[C:16]([CH2:19][CH2:20][CH2:21][C:22]([N:24]1[CH2:28][C@@H:27]([P:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:26]([P:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:25]1)=O)(O)=O>CN(C1C=CN=CC=1)C.ClCCl>[CH2:28]1[N:24]([CH2:22][C:21]2[CH:2]=[CH:1][CH:16]=[CH:19][CH:20]=2)[CH2:25][C@@H:26]([P:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:27]1[P:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 23414420HCID 23414420, compound

Product 1

HCID 10985824(3R,4R)-1-Benzyl-3,4-bis(diphenylphosphanyl)pyrrolidineYield 369.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Preparation of polyester-supported DUGPHOS ligand. DCC (40 mg, 0.194 mmol) was added to a mixture of the above OH-terminating polyester (Mw=4200, 0.390 g, ~0.186 mmol OH), (3R, 4R)-N-(4-carboxybutanoyl)-3,4-bis(diphenylphosphanyl)pyrrolidine (120 mg, 0.223 mmol), and DMAP (5 mg, 0.041 mmol) in dichloromethane (20 mL). The reaction mixture was stirred for 12 h at ambient temperature and the urea precipitate was removed by filtration. Methanol was then slowly added to the resulting filtrate under stirring, and the precipitated polyester-supported DEGPHOS ligand was then isolated by filtration, and washed with cold methanol and dried in vacuo to give 380 mg polymeric DEGPHOS ligand (96% theoretical yield): ##STR16## The analytical data for this new material are as follows:

Workup

  1. customthe urea precipitate was removed by filtration
  2. additionMethanol was then slowly added to the resulting filtrate
  3. stirringunder stirring
  4. customwas then isolated by filtration
  5. washwashed with cold methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-590c3f0ff9b14b1a8cec2cf735501300
Source dataset
uspto-grants-1999_11
Patent number
US05990318

Reaction notes

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