Hydrochloric Acid → HCID 67371255, compound

HRID 1677088Notes

Reaction equation

HRID 1677088 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CCOCC.C([O:12][C:13]([C@H:15]1[CH2:19][CH2:18][C@@H:17]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[C:22]([F:28])[CH:21]=2)[N:16]1[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O)C.Cl>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C>[CH2:29]([N:16]1[C@H:17]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[C:22]([F:28])[CH:21]=2)[CH2:18][CH2:19][C@@H:15]1[C:13]1([OH:12])[CH2:2][CH2:1]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67374843HCID 67374843, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 67371255HCID 67371255, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere and at room temperature, ethyl magnesium bromide (8.49 mL, tetrahydrofuran 1M solution) was added dropwise over 1 hour into an ether (10 mL) solution of (2R,5S)-1-benzyl-5-(3,4,5-trifluorophenyl)pyrrolidine-2-carboxylic acid ethyl ester (1.03 g) and titanium tetraisopropoxide (209 μL). The resultant was stirred at the same temperature for 15 hours. The reaction solution was ice-cold, and 1 N hydrochloric acid was added, stirring was continued for 30 minutes at the same temperature. Ethyl acetate was added, and the organic layer was partitioned, and after washing the organic layer with brine, the resultant was dried with magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography, and the title compound (602 mg) was obtained. The physical property values are as follows.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 30 minutes at the same temperature
  4. customthe organic layer was partitioned
  5. washafter washing the organic layer with brine
  6. dry with materialthe resultant was dried with magnesium sulfate
  7. customThe solvent was removed under a vacuum
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f4d71c3b61454f9eaae2e62fa6708d95
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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