Potassium Carbonate → (9aS)-8-[3-(methyloxy)-4-nitrophenyl]octahydropyrazino[2,1-c][1,4]oxazine

HRID 419446노트

반응식

HRID 419446 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].Cl.Cl.[CH2:15]1[C@@H:20]2[CH2:21][NH:22][CH2:23][CH2:24][N:19]2[CH2:18][CH2:17][O:16]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:22]2[CH2:23][CH2:24][N:19]3[C@H:20]([CH2:15][O:16][CH2:17][CH2:18]3)[CH2:21]2)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 66649934(S)-Octahydropyrazino[2,1-C][1,4]oxazine dihydrochloride

생성물 1

HCID 59452846(9aS)-8-[3-(methyloxy)-4-nitrophenyl]octahydropyrazino[2,1-c][1,4]oxazine수율 76%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

5-Fluoro-2-nitrophenyl methyl ether (Example 22, step A) (0.318 g, 1.86 mmol), (9aS)-octahydropyrazino[2,1-c][1,4]oxazine dihydrochloride (Example 87, step G) (0.190 g, 0.880 mmol) and K2CO3 (0.614 g, 4.44 mmol) were stirred in DMSO (4 mL) at rt overnight. The reaction was diluted with EtOAc, washed with H2O (3×), dried (MgSO4) and concentrated. Purification by flash chromatography provided the title compound of step A (0.196 g, 0.660 mmol, 76%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.12-2.24 (m, 3H), 2.68 (d, J=11.4 Hz, 1H), 2.78-2.84 (m, 1H), 2.96 (td, J=12.3, 3.3 Hz, 1H), 3.10-3.18 (m, 1H), 3.52 (td, J=11.5, 2.4 Hz, 1H), 3.75 (dd, J=11.0, 2.9 Hz, 3H), 3.82-3.88 (m, 1H), 3.89 (s, 3H), 3.97 (d, J=13.9 Hz, 1H), 6.52 (d, J=2.6 Hz, 1H), 6.59 (dd, J=9.2, 2.6 Hz, 1H), 7.87 (d, J=9.5 Hz, 1H).

후처리

  1. washwashed with H2O (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-0ed530b9786142c4a8dc34e19752a09c
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

반응 노트

불러오는 중…