Toluene → (S)-5-benzyl-1-((1S,2S)-2-hydroxycyclopent-3-enecarbonyl)pyrrolidin-2-one

HRID 56402Notes

Reaction equation

HRID 56402 reaction equation
C([C@@H:4]([C@@H:20]([OH:29])/[CH:21]=[CH:22]/[C:23]1C=CC=CC=1)[C:5]([N:7]1[C@H:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10]O[C:8]1=[O:19])=[O:6])C=C.[C:30]1(C)C=CC=CC=1>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[CH2:12]([C@H:11]1[N:7]([C:5]([C@H:4]2[CH2:23][CH:22]=[CH:21][C@@H:20]2[OH:29])=[O:6])[C:8](=[O:19])[CH2:30][CH2:10]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 67113561(R)-3-((2S,3S,E)-2-allyl-3-hydroxy-5-phenylpent-4-enoyl)-4-benzyloxazolidin-2-one

Product 1

HCID 118036214(S)-5-benzyl-1-((1S,2S)-2-hydroxycyclopent-3-enecarbonyl)pyrrolidin-2-oneYield 87%

Reagents, catalysts & solvents 1

HCID 178425456HCID 178425456, compoundCatalyst

Procedure

A solution of (R)-3-((2S,3S,E)-2-allyl-3-hydroxy-5-phenylpent-4-enoyl)-4-benzyloxazolidin-2-one (50 g, 128 mmol) and Grubbs 2nd generation catalyst (5.4 g, 6.4 mmol) in toluene (300 mL) was degassed with nitrogen three times, and stirred at room temperature overnight. The reaction mixture was then concentrated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:4) to afford the title compound (32 g, 87%) as a dark brown oil, which solidified upon standing. MS (ES+) C17H19NO3 requires: 285, found: 270 [M+H−H2O]+.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:4)

Sources & evidence

ORD record
ord-314a02587ea64f21aa1c2b57fa79164c
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

Loading…