Imidazole → HCID 67490801, compound

HRID 1917326Notes

Reaction equation

HRID 1917326 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:19][CH2:20][C:21]1([C@H:24]2[CH2:28][C:27](=[O:29])[N:26]([C@H:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH3:31])[CH2:25]2)[CH2:23][CH2:22]1.N1C=CN=C1>CN(C)C=O.C(OCC)(=O)C>[O:19]([CH2:20][C:21]1([C@H:24]2[CH2:28][C:27](=[O:29])[N:26]([C@H:30]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH3:31])[CH2:25]2)[CH2:22][CH2:23]1)[Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 67490989HCID 67490989, compound

Product 1

HCID 67490801HCID 67490801, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyldiphenylsilyl chloride (2.83 ml, 10.88 mmol) was added to a solution of (3R)-3-[1-(hydroxymethyl)cyclopropan-1-yl]-5-oxo-1-[(1S)-1-phenylethyl]pyrrolidine (2.35 g, 9.06 mmol) and imidazole (925 mg, 13.59 mmol) in N,N-dimethylformamide (30 mL), and the mixture was stirred at room temperature for 20 hours. The reaction solution was diluted with ethyl acetate (150 mL), washed with water (50 mL×2) and brine (50 mL×2), dried over anhydrous sodium sulfate, and then filtered. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19→1:9→1:4→1:1) to give 3.88 g (86%) of the title compound as a colorless transparent gummy solid.

Workup

  1. washwashed with water (50 mL×2) and brine (50 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19→1:9→1:4→1:1)

Sources & evidence

ORD record
ord-1da84cca2732423889265a3d992d4998
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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