Ethyl Acetate → Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]-3-hydroxyazetidine-1-carboxylate

HRID 605761Notes

Reaction equation

HRID 605761 reaction equation
O1CCOC1CC=C1C[N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:9]1.C[N+]1([O-])CC[O:26]CC1.[C:30]([O:33][CH2:34][CH3:35])(=[O:32])[CH3:31].[CH3:36][C:37]([CH3:39])=[O:38].O>[Os](=O)(=O)(=O)=O>[O:33]1[CH2:34][CH2:35][O:32][CH:30]1[CH2:31][CH:36]([C:37]1([OH:38])[CH2:9][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:39]1)[OH:26]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 67051614Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)ethylidene]azetidine-1-carboxylate

Product 1

HCID 67051562Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]-3-hydroxyazetidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)ethylidene]azetidine-1-carboxylate (220 mg, 0.761 mmol), and 4-methylmorpholine N-oxide (287 mg, 2.45 mmol) were dissolved in acetone/water (4:1; 10 mL) and osmium tetroxide (4 wt. % in water; 0.05 mL) was added. The solution was stirred at ambient for 20 h, then was quenched with saturated sodium bisulfite (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 phenylmethyl 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]-3-hydroxyazetidine-1-carboxylate (244 mg, 0.755 mmol, 99% yield): 1H NMR (400 MHz, CDCl3): 7.38-7.28 (m, 5H), 5.11-5.07 (m, 3H), 4.14-4.01 (m, 4H), 3.96-3.86 (m, 5H), 3.47 (d, 1H), 2.97-2.94 (m, 1H), 1.98-1.84 (m, 2H).

Workup

  1. customwas quenched with saturated sodium bisulfite (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-7bdec939f66049cba5884b8cced76123
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

Loading…