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

HRID 1478427ノート

反応式

HRID 1478427 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c23f8b9a0961458fa39b640b967e6802
出典データセット
uspto-grants-2016_08
特許番号
US09403839B2

反応ノート

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