Sodium Hypochlorite → Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylate

HRID 77569노트

반응식

HRID 77569 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 23665760Sodium HypochloriteHCID 74074414Benzyl N-allyl-N-[2-hydroxyiminoethyl]carbamate

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-[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-79559e19ee9047a3b0264ef612760d7f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841293B1

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