m-Chloroperbenzoic acid → Tert-butyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylate

HRID 605685노트

반응식

HRID 605685 반응식
[CH2:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)(Cl)Cl>[O:18]1[C:2]2([CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]2)[CH2:1]1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 55269097tert-Butyl 3-methylideneazetidine-1-carboxylate

생성물 1

HCID 66521770Tert-butyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylate수율 51%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 1,1-dimethylethyl 3-methylideneazetidine-1-carboxylate (2.96 g, 17.5 mmol) in chloroform (180 mL) was added 3-chloroperoxybenzoic acid (77%, 13.9 g, 62.0 mmol), and the resulting mixture was stirred at room temperature for 2 days. The reaction mixture was quenched with a 1:1 mixture (150 mL) of 10% sodium thiosulfate and saturated sodium bicarbonate solutions. The organic portion was isolated, dried over sodium sulfate, filtered and concentrated to give an oily residue which was then purified by flash chromatography (15-50% ethyl acetate-hexanes) to give 1,1-dimethylethyl 1-oxa-5-azaspiro[2.3]hexane-5-carboxylate (1.65 g, 51%), GC-MS for C9H15NO3: 185.

후처리

  1. customThe reaction mixture was quenched with a 1:1 mixture (150 mL) of 10% sodium thiosulfate and saturated sodium bicarbonate solutions
  2. customThe organic portion was isolated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oily residue which
  7. customwas then purified by flash chromatography (15-50% ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-fd69c6c51f7141788107b5c6876a5e2c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915250B2

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