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

HRID 1197825노트

반응식

HRID 1197825 반응식
[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

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 68352alpha-Methylene butyrolactoneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3cd9bee9312a45d9acd0edb75624b503
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278170

반응 노트

불러오는 중…