Trifluoroacetic acid → 1-Oxa-9-azaspiro[5.5]undec-2-en-4-one

HRID 1478427노트

반응식

HRID 1478427 반응식
[O:1]=[C:2]1[CH:19]=[CH:18][O:17][C:4]2([CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:9]1[C:4]2([O:17][CH:18]=[CH:19][C:2](=[O:1])[CH2:3]2)[CH2:5][CH2:6][NH:7][CH2:8]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 897085271-Oxa-9-azaspiro[5.5]undec-2-ene-9-carboxylic acid, 4-oxo-, 1,1-dimethylethyl ester

생성물 1

HCID 897083431-Oxa-9-azaspiro[5.5]undec-2-en-4-one수율 239.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 8-oxo-11-oxa-3-azaspiro[5.5]undec-9-ene-3-carboxylate (200 mg, 0.748 mmol) in CH2Cl2 (2.4 mL) was added TFA (0.6 mL, 7.8 mmol). The mixture was stirred at room temperature for 15 min. Solvent was removed. The crude material was evaporated again from toluene (2×) and dried under high vacuum overnight to provide 11-oxa-3-azaspiro[5.5]undec-9-en-8-one (300 mg). 1H NMR (400 MHz, CDCl3) δ 7.34 (d, J=6.1 Hz, 1H), 5.57 (d, J=6.1 Hz, 1H), 3.45 (d, J=11.7 Hz, 2H), 3.34 (dd, J=24.1, 12.7 Hz, 2H), 2.67 (s, 2H), 2.38 (d, J=14.6 Hz, 2H), 1.98 (td, J=14.8, 4.8 Hz, 2H). ESI-MS m/z calc. 167.09, found 168.2 (M+1)+; Retention time: 0.17 minutes (3 minute run).

후처리

  1. customSolvent was removed
  2. customThe crude material was evaporated again from toluene (2×)
  3. customdried under high vacuum overnight

출처 및 근거

ORD 기록
ord-c23f8b9a0961458fa39b640b967e6802
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403839B2

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