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

HRID 605725ノート

反応式

HRID 605725 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 30318Osmium Tetroxide触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4c8d2d9f69c048fdbef63575ccda26c0
出典データセット
uspto-grants-2011_03
特許番号
US07915250B2

反応ノート

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