Triethylamine → cis-3-hydroxy-4-phenylazetidin-2-one

HRID 900503Notes

Reaction equation

HRID 900503 reaction equation
C[Si](C)(C)[N:3]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]([O:13][Si](C)(C)C)[C:4]1=[O:18].C(N(CC)CC)C.C(OCC)(=O)C>CO.C[Si](C)(C)Cl>[OH:13][C@H:5]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:3][C:4]1=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11988558HCID 11988558, compound

Product 1

HCID 10219588cis-3-hydroxy-4-phenylazetidin-2-oneYield 94%

Reagents, catalysts & solvents 2

HCID 6397ChlorotrimethylsilaneCatalystHCID 887MethanolSolvent

Procedure

To a heterogeneous solution of N-trimethylsilyl-3-trimethylsiloxy-4-phenyl-azetidin-2-one (150 g, 0.49 mol) in methanol (500 mL) was added a catalytic amount of trimethylchlorosilane (1.089, g 1 mmol) and the mixture was stirred at ambient temperature to give a clear solution. Thin layer chromatography (TLC) monitoring of the reaction eluting with ethyl acetate and hexanes (3:1) indicated that complete conversion was achieved after 15 minutes. The reaction mixture was quenched with triethylamine (10.1 g, 0.1 mol) and the methanol was removed under rotary evaporation at 40° C. until crystals formed. Ethyl acetate (300 mL) was added and the evaporation was continued to remove the remaining methanol to give a thick slurry before cooling to 0 to 5° C. for 20 minutes. The white crystals were collected via vacuum filtration following by washing with cold 0° C. ethyl acetate (75 mL) and dried to constant weight of 75 g (94% yield) of the desire product described previously.

Workup

  1. customto give a clear solution
  2. washThin layer chromatography (TLC) monitoring of the reaction eluting with ethyl acetate and hexanes (3:1)
  3. customthe methanol was removed under rotary evaporation at 40° C. until crystals
  4. customformed
  5. customthe evaporation
  6. customto remove the remaining methanol
  7. customto give a thick slurry
  8. temperaturebefore cooling to 0 to 5° C. for 20 minutes
  9. filtrationThe white crystals were collected via vacuum filtration
  10. washby washing with cold 0° C. ethyl acetate (75 mL)

Sources & evidence

ORD record
ord-26e32556e6ea43dd84963ed19f40ce61
Source dataset
uspto-grants-2008_04
Patent number
US07358378B2

Reaction notes

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