Tetrahydrofuran → HCID 18386973, compound

HRID 2298508Notes

Reaction equation

HRID 2298508 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C[O:24]CC1>>[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH:16]([OH:24])[C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 18386974HCID 18386974, compound

Product 1

HCID 18386973HCID 18386973, compoundYield 43%

Procedure

To a solution of methyl 4-(3-tert-butoxycarbonylphenyl)butanoate (200 mg, 0.71 mmol) in THF (2 ml) at −78° C. was added dropwise potasium bis(trimethyl)amide (0.5 M in toluene, 1.6 ml, 0.8 mmol). The mixture was stirred at this temperature for 0.5 hours and treated with dropwise addition of a solution of trans-2-phenylsulfonyl-3-phenyloxaziridine (223 mg, 0.8 mmol) in THF (2 ml). The mixture was stirred at −78° C. for 3 hours, quenched with aqueous ammonium chloride, warmed room temperature and diluted with ethyl acetate. The organic phase was washed with aqueous ammonium chloride, brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane:ethyl acetate=9:1) to give the title compound (90 mg, 43%) as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred at −78° C. for 3 hours
  2. customquenched with aqueous ammonium chloride
  3. additiondiluted with ethyl acetate
  4. washThe organic phase was washed with aqueous ammonium chloride, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-2fd8ba56420f4e23830878ab0c7f308a
Source dataset
uspto-grants-2002_12
Patent number
US06492550B2

Reaction notes

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