Trifluoroacetic acid → 7-Benzyl-1-cyano-2-oxa-7-azabicyclo[3.3.0]octane

HRID 53875노트

반응식

HRID 53875 반응식
[O:1]1[CH2:5][CH2:4][CH:3]=[C:2]1[C:6]#[N:7].C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH2:22]([N:29]([CH2:35]OC)[CH2:30][Si](C)(C)C)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([N:29]1[CH2:30][C:2]2([C:6]#[N:7])[CH:3]([CH2:4][CH2:5][O:1]2)[CH2:35]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 136240424,5-Dihydrofuran-2-carbonitrile

생성물 1

HCID 217047477-Benzyl-1-cyano-2-oxa-7-azabicyclo[3.3.0]octane

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

14.4 g (0.15 mol) of 4,5-dihydrofuran-2-carbonitrile are introduced in 300 ml of absolute methylene chloride, 1.8 g of triethylamine and 1.8 g of trifluoroacetic acid are added, and the mixture is warmed to 40° C. 42.6 g (0.15 mol) of N-benzyl-N-methoxymethyl-N-trimethylsilylmethylamine are added dropwise to this mixture which is then stirred at 40° C. for 15 hours. It is then washed with 50 ml of saturated sodium hydrogen carbonate solution, dried over MgSO4, concentrated and distilled twice. Yield: 9.3 g (22.5% of theory) Boiling point: 120°-125° C./0.06 mbar The product is 83% pure by gas chromatography.

후처리

  1. washIt is then washed with 50 ml of saturated sodium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. distillationdistilled twice

출처 및 근거

ORD 기록
ord-4ef7306ed9f84164932eba1e3b7716c2
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621105

반응 노트

불러오는 중…