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

HRID 1587368ノート

反応式

HRID 1587368 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収率 81.4%

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 (D8, 160 g of 75% purity, assume 0.51 mole) and α-methylene-γ-butyrolactone (D10, 50 g, 0.51 mole) in dichloromethane (1 liter) under nitrogen was cooled to 0° C. and then treated with a 1 M solution of trifluoroacetic acid in dichloromethane (50 ml, 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 (D11) 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-dd27cedae0a845dbb55c30197aa0b125
出典データセット
uspto-grants-1993_06
特許番号
US05217975

反応ノート

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