1,2-Bis(diphenylphosphino)ethane → Ethyl cis-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine-3-carboxylate

HRID 1954623Notes

Reaction equation

HRID 1954623 reaction equation
C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:29]([N:36]1[CH2:40][C:39]([C:41]2([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:43][CH2:42]2)=[C:38]([C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO>[CH2:29]([N:36]1[CH2:40][C@H:39]([C:41]2([NH:44][C:45]([O:47][C:48]([CH3:50])([CH3:51])[CH3:49])=[O:46])[CH2:42][CH2:43]2)[C@H:38]([C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 742671,2-Bis(diphenylphosphino)ethaneHCID 21261012Ethyl 1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-pyrroline-3-carboxylate

Product 1

HCID 69563544Ethyl cis-1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine-3-carboxylateYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen gas stream, bis(bicyclo[2.2.1]hepta-2,5-diene)rhodium (I) perchlorate (54.5 mg, 0.14 mmol) and 1,2-bis(diphenylphosphino)ethane (67.4 mg, 0.17 mmol) were dissolved in degassed methanol (25 ml) and stirred at room temperature for 10 minutes. To this catalyst solution was added a solution of ethyl 1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-pyrroline-3-carboxylate (1.090 g, 2.820 mmol) in dry and degassed methanol (15 ml). The thus obtained liquid reaction mixture was then stirred under a hydrogen atmosphere (1 kg/cm2) at room temperature for 2.5 hours. After adding active carbon (1 g), the liquid reaction mixture was allowed to stand at room temperature for 30 minutes and then filtered-through celite (washed with methanol). The filtrate was concentrated under reduced pressure and the residue was subjected to flash silica gel column chromatography (eluent:n-hexane:ethyl acetate=5:1) to obtain 1.071 g (97.8%) of the title compound as colorless crystals.

Workup

  1. customin dry
  2. customdegassed methanol (15 ml)
  3. customThe thus obtained liquid reaction mixture
  4. stirringwas then stirred under a hydrogen atmosphere (1 kg/cm2) at room temperature for 2.5 hours
  5. additionAfter adding active carbon (1 g)
  6. customthe liquid reaction mixture
  7. waitto stand at room temperature for 30 minutes
  8. filtrationfiltered-through
  9. washcelite (washed with methanol)
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ed967e933c6f4882b70c4a97318c5582
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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