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

HRID 1808985노트

반응식

HRID 1808985 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 30318Osmium Tetroxide촉매

실험 절차

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 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 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).

후처리

  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

출처 및 근거

ORD 기록
ord-5ce6ca650a0e460e90db2c5491c1aeb9
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362002B2

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