Trifluoroacetic acid → 6-Benzyl-8-nitro-2-oxa-6-aza-spiro[3.4]octane

HRID 539981ノート

反応式

HRID 539981 の反応式
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH:20]=[C:21]1[CH2:24][O:23][CH2:22]1)([O-:19])=[O:18].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH:20]([N+:17]([O-:19])=[O:18])[C:21]2([CH2:24][O:23][CH2:22]2)[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 533465963-(Nitromethylidene)oxetane

生成物 1

HCID 712547596-Benzyl-8-nitro-2-oxa-6-aza-spiro[3.4]octane収率 67.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of benzyl-methoxymethyl-trimethylsilanylmethyl-amine (3.0 g, 12.6 mmol) and 3-nitromethylene-oxetane (1.38 g, 12.0 mmol) in dichloromethane (60 mL) was added trifluoroacetic acid (0.93 mL, 12.6 mmol) dropwise. The mixture was stirred at room temperature for 2 hours, quenched with sodium carbonate, extracted with dichloromethane. The organic layer was dried over sodium sulfate, concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 2 g of product as colorless oil. It was used for next step without further purification.

後処理

  1. customquenched with sodium carbonate
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-1685039ec598424198255aa497d5deb0
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

反応ノート

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