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

HRID 1618987ノート

反応式

HRID 1618987 の反応式
[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

参加物

4

反応物 2

HCID 23635904HCID 23635904、化合物HCID 23665760Sodium Hypochlorite

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-936542d4f3f44d0aa28344de91b67308
出典データセット
uspto-grants-2014_07
特許番号
US08772282B2

反応ノート

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