Trifluoroacetic anhydride → N-(3-(1Admantyl)-4-isopropoxyphenethyl)-2,2,2-trifluoro-acetamide

HRID 710451노트

반응식

HRID 710451 반응식
[C:1]12([C:11]3[CH:12]=[C:13]([CH2:21][CH2:22][NH2:23])[CH:14]=[CH:15][C:16]=3[O:17][CH:18]([CH3:20])[CH3:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[O:24](C(C(F)(F)F)=O)[C:25]([C:27]([F:30])([F:29])[F:28])=O>>[C:1]12([C:11]3[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=3[O:17][CH:18]([CH3:19])[CH3:20])[CH2:21][CH2:22][NH:23][C:25](=[O:24])[C:27]([F:30])([F:29])[F:28])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

참가 물질

3

반응물 2

HCID 9845Trifluoroacetic anhydrideHCID 667263922-(3-(1-Admantyl)-4-isopropoxyphenyl)ethanamine

생성물 1

HCID 87126503N-(3-(1Admantyl)-4-isopropoxyphenethyl)-2,2,2-trifluoro-acetamide수율 82.4%

실험 절차

To a stirred solution of 2-(3-(1-Admantyl)-4-isopropoxyphenyl)ethanamine (0.28 g, 0.86 mmol) in a mixture of solvents (CH2Cl2:Et3N: 10:0.5 ml) (CF3CO)2O (0.157 ml) was added at 0° C. under N2. The reaction mixture was stirred for 2 h at room temperature, then the solvent was evaporated to dryness. The residue was diluted to 50 ml with EtOAc and washed with 1M HCl. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title product (0.29 g, 82.4%). 1H-NMR (CDCl3) 1.37 (d, 6H, J=6 Hz); 1.67-1.75 (m, 6H); 2.04-2.23 (m, 9H); 2.78 (tr, 2H, J=6.84 Hz); 3.53-3.59 (m, 2H); 4.57-4.63 (m, 1H); 6.77 (d, 1H, J=8.32 Hz); 6.92 (dd, 1H, J=2.21, 8.27 Hz); 6.98 (d, 1H, J=2.21 Hz).

후처리

  1. additionwas added at 0° C. under N2
  2. customthe solvent was evaporated to dryness
  3. additionThe residue was diluted to 50 ml with EtOAc
  4. washwashed with 1M HCl
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-0eb14a34d4b94b729ae8c5e67395e459
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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