Trifluoroacetic acid → 7-Benzyl-2-oxa-7-azaspiro[4.4]nonan-1-one

HRID 1197825ノート

反応式

HRID 1197825 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.[CH2:17]=[C:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH2:17][C:18]2([C:19](=[O:20])[O:21][CH2:22][CH2:23]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 68352alpha-Methylene butyrolactoneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

生成物 1

HCID 41971377-Benzyl-2-oxa-7-azaspiro[4.4]nonan-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A stirred solution of N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (D12, 160 g of 75% purity, assume 0.51 mole) and α-methylene-γ-butyrolactone (D14, 50 g, 0.51 mole) in dichloromethane (11 L) under nitrogen was cooled to 0° C. and then treated with a 1M solution of trifluoroacetic acid in dichloromethane (50ml, 0.05 mole), keeping the temperature below 5° C. The reaction mixture was allowed to warm to room temperature over 2 h, then washed with saturated sodium bicarbonate solution. The aqueous wash was extracted with dichloromethane and the organic solutions then combined, washed with brine, dried (Na2SO4) and concentrated in vacuo to leave a pale yellow oil. This was distilled in vacuo to give the title compound (D15) as a colourless oil (96 g, 81%) b.p. 160°-170° C. at 1 mmHg.

後処理

  1. customthe temperature below 5° C
  2. washwashed with saturated sodium bicarbonate solution
  3. washThe aqueous wash
  4. extractionwas extracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto leave a pale yellow oil
  9. distillationThis was distilled in vacuo

出典と根拠

ORDレコード
ord-3cd9bee9312a45d9acd0edb75624b503
出典データセット
uspto-grants-1994_01
特許番号
US05278170

反応ノート

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