4-(4-Bromophenyl)-4-fluoro-1-methylpiperidine → 4-Fluoro-1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine

HRID 447316노트

반응식

HRID 447316 반응식
C(OC1CCN([C:11]2[CH:16]=[CH:15][C:14]([B:17]3[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]3)=[CH:13][CH:12]=2)CC1)(=O)C.BrC1C=CC([C:33]2([F:40])[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)=CC=1>CCOC(C)=O.O>[F:40][C:33]1([C:11]2[CH:12]=[CH:13][C:14]([B:17]3[O:18][C:19]([CH3:24])([CH3:25])[C:20]([CH3:22])([CH3:23])[O:21]3)=[CH:15][CH:16]=2)[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]1

참가 물질

5

반응물 2

HCID 582665264-(4-Bromophenyl)-4-fluoro-1-methylpiperidineHCID 667303481-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetate

생성물 1

HCID 584862834-Fluoro-1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

The title compound was synthesized according to the method described for the synthesis of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetate, except substituting 4-(4-bromophenyl)-4-fluoro-1-methylpiperidine (133 mg, 0.49 mmol). The reaction was then allowed to cool to room temperature and was diluted with EtOAc and water was added. The resulting mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried over MgSO4 and concentrated to give the title compound as a brown solid (281 mg, used without further purification). 1H NMR (400 MHz, MeOD) δ 7.76 (d, J=7.7 Hz, 2H), 7.41 (d, J=7.8 Hz, 2H), 2.94-2.91 (m, 2H), 2.59 (t, J=12.0 Hz, 2H), 2.45 (s, 3H), 2.30-2.22 (m, 1H), 2.20-2.12 (m, 1H), 2.01-1.95 (m, 2H); 19F NMR (400 MHz, MeOD) δ—162.38; MS ESI 320.1 [M+H]+, calcd for [C18H27BFNO2+H]+ 320.21.

후처리

  1. customThe title compound was synthesized
  2. additionwas added
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-22d879af762d433e99a5405b3274072e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481533B2

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