Ethanol → HCID 58580629, compound

HRID 1920799Notes

Reaction equation

HRID 1920799 reaction equation
[Si:1]([O:8][C@H:9]([CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([F:37])[CH:31]=1)[CH2:10][O:11][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][OH:22])[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:38]([O:40][C:41](=[O:45])[CH:42]=[N+]=[N-])[CH3:39].C(O)C>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[Si:1]([O:8][C@H:9]([CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([F:37])[CH:31]=1)[CH2:10][O:11][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][O:22][CH2:42][C:41]([O:40][CH2:38][CH3:39])=[O:45])[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 12192Ethyl diazoacetateHCID 58580717HCID 58580717, compound

Product 1

HCID 58580629HCID 58580629, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

2-{2-[(1R)-1-({(2R)-2-{[Tert-butyl(dimethyl)silyl]oxy}-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]propyl}oxy)ethyl]phenyl}ethanol (545 mg, 1.03 mmol), which had been obtained in Example 180 (180d), was dissolved in methylene chloride (5 mL), added with rhodium diacetate dimer (46 mg, 0.10 mmol) and ethyldiazoacetate (267 μL, 2.58 mmol) at 0° C., and stirred for 1.5 hours. Ethanol was added to the reaction solution to terminate the reaction. The solvent was distilled off under reduced pressure. The residue was purified by basic silica gel chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a colorless oily substance (565 mg, yield 89%).

Workup

  1. customto terminate
  2. customthe reaction
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe residue was purified by basic silica gel chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d85dda5cc88c4f189282ff91271fd4f2
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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