HCID 23635904, 화합물 → Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylate

HRID 470211노트

반응식

HRID 470211 반응식
[CH2:1]([N:4]([CH2:15]/[CH:16]=[N:17]/[OH:18])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].Cl[O-].[Na+]>ClCCl>[N:17]1[O:18][CH2:3][CH:2]2[CH2:1][N:4]([C:5]([O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:14])[CH2:15][C:16]=12

참가 물질

4

반응물 2

HCID 23635904HCID 23635904, 화합물HCID 23665760Sodium Hypochlorite

생성물 1

HCID 86697896Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylate수율 75.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of benzyl N-allyl-N-[(2E)-2-hydroxyiminoethyl]carbamate (24 g, 96.6 mmol) in dichloromethane (338 mL) is treated drop wise over 10 minutes with a 5% w/w aqueous solution of sodium hypochlorite (106.08 mmol, 143.06 mL). The resultant mixture is stirred at room temperature overnight. The reaction is quenched with a 40% aqueous solution of sodium bisulfite (7 g). The organic layer is separated, dried over magnesium sulfate, and concentrated under vacuum. The crude product is purified over silica gel eluting with 5% ethyl acetate in hexanes to give the title compound (18 g, 75%). ES/MS (m/e): 247 (M+H).

후처리

  1. customThe reaction is quenched with a 40% aqueous solution of sodium bisulfite (7 g)
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product is purified over silica gel eluting with 5% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-2fa4fe1c60d140f6bfb2ac448c0bf1eb
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

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