Toluene → HCID 22865001, compound

HRID 1078717Notes

Reaction equation

HRID 1078717 reaction equation
C(N(CC)CC)C.C1(C)C=CC=CC=1.[C:15]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][C@H:23]1[C:35](=[O:41])[CH2:36][C:37](=[O:40])[NH:38][CH3:39])=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1CC=CCCC=C1.Cl[Ru]Cl.C(O)C>[C:15]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][Si:28]([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:29])[CH3:30])[CH2:24][C@H:23]1[CH:35]([OH:41])[CH2:36][C:37](=[O:40])[NH:38][CH3:39])=[O:21])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 1140TolueneHCID 8471TriethylamineHCID 22865011HCID 22865011, compound

Product 1

HCID 22865001HCID 22865001, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 1100043550982-12-2CatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, (1,5-cyclooctadiene)ruthenium(II) chloride polymer (10 mg, 3.6×10-2 mmol), (S)-(-)-bis(diphenylphosphino)-1,1'-binaphthyl (24 mg, 3.6×10-2 mmol), triethylamine (0.1 ml, 6.5×10-1 mmol) and toluene (5 ml) were stirred in a sealed tube at 140° C. for 6 h. The solvent was removed in vacuo from the obtained red solution. To the residue was added a tetrahydrofuran (5 ml)--ethanol (10 ml) solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[2-(N-methylcarbamoyl)-1-oxoethyl]pyrrolidine (1.5 g, 3.9 mmol). The mixture was stirred under a hydrogen pressure of 4 kg/cm2 at 80° C. for 22 h. Then, the reaction solution was concentrated. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, heptane-ethyl acetate=3:1→1:3) to give the title compound [1.19 g, yield: 79%; by high performance liquid column chromatography YMC PACKED COLUMN, AQ-32 S-5 120A ODS, developer:acetonitrile--water 70:30, detection at 210 nm (R)-isomer (polar compound):(S)-isomer (less polar compound)=1.89:1].

Workup

  1. customThe solvent was removed in vacuo from the obtained red solution
  2. additionTo the residue was added a tetrahydrofuran (5 ml)
  3. concentrationThen, the reaction solution was concentrated

Sources & evidence

ORD record
ord-a0cedf73d63646afb4d782b3dfd7290c
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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