Ethyl Acetate → 1-Azetidinecarboxylic acid, 3-hydroxy-3-(1-hydroxyethyl)-, 1,1-dimethylethyl ester

HRID 605725Notes

Reaction equation

HRID 605725 reaction equation
C(=C1C[N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C1)C.C[N+]1([O-])CC[O:18][CH2:17][CH2:16]1.C(OCC)(=O)C.[CH3:28][C:29]([CH3:31])=[O:30].O>[Os](=O)(=O)(=O)=O>[OH:30][C:29]1([CH:17]([OH:18])[CH3:16])[CH2:31][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[CH2:28]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 52180841tert-Butyl 3-ethylideneazetidine-1-carboxylate

Product 1

HCID 670516151-Azetidinecarboxylic acid, 3-hydroxy-3-(1-hydroxyethyl)-, 1,1-dimethylethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

1,1-Dimethylethyl 3-ethylideneazetidine-1-carboxylate (506 mg, 2.76 mmol), and 4-methylmorpholine N-oxide (1.04 g, 8.89 mmol) were dissolved in acetone/water (4:1; 30 mL) and osmium tetroxide (2.5 wt. % in t-butanol; 0.2 mL) was added. The solution was stirred at ambient for 5 days, then was quenched with saturated sodium bisulfate (2 mL) and concentrated in vacuo. The residue was partitioned between ethyl acetate and brine. The aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, ethyl acetate) gave 1,1-dimethylethyl 3-hydroxy-3-(1-hydroxyethyl)azetidine-1-carboxylate (375 mg, 1.73 mmol, 63% yield): 1H NMR (400 MHz, CDCl3): 4.00-3.77 (m, 5H), 2.65 (br s, 1H), 1.86, (br s, 1H), 1.44 (s, 9H), 1.25 (d, 3H).

Workup

  1. customwas quenched with saturated sodium bisulfate (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and brine
  4. extractionThe aqueous portion was extracted with ethyl acetate
  5. washThe combined organic portion was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c8d2d9f69c048fdbef63575ccda26c0
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

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