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3,3-Diphenylpiperidin-2-one → HCID 67445694, 화합물

HRID 1667208
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HRID 1667208 반응식
CC(C)([O-])C.[K+].[C:7]1([C:13]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:17][CH2:16][NH:15][C:14]2=[O:19])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:27][C:28]([N:30]([CH:41]1[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]1)[C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=1)=[O:29]>O1CCCC1.[Cl-].[Na+].O>[O:19]=[C:14]1[C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][CH2:17][CH2:16][N:15]1[CH2:27][C:28]([N:30]([CH:41]1[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]1)[C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:38])([F:39])[F:40])=[CH:33][CH:32]=1)=[O:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 3211653,3-Diphenylpiperidin-2-oneHCID 23665647Potassium tert-butoxideHCID 67445908tert-butyl 4-(2-bromo-N-(4-(trifluoromethyl)phenyl)acetamido)piperidine-1-carboxylate

생성물 1

HCID 67445694HCID 67445694, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 57417360
Sodium chloride; water
용매

실험 절차

A solution of potassium tert-butoxide (1.0 M in tetrahydrofuran, 0.70 mL, 0.70 mmol) was added dropwise via syringe to a suspension of the product of Example 68C (147 mg, 0.587 mmol) in anhydrous tetrahydrofuran (5 mL) at ambient temperature. The reaction mixture was stirred for 45 minutes, and then a solution of the product of Example 166B (273 mg, 0.587 mmol) in 3 mL tetrahydrofuran was added. The reaction was allowed to proceed for 1 hour at ambient temperature, then poured into brine. The product was extracted with ethyl acetate and the combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 25%-75% ethyl acetate/hexanes, 0-15 minutes, 30 mL/minute) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.69 (d, J=8.3, 2H), 7.35 (d, J=8.2, 2H), 7.32-7.15 (m, 10H), 4.86-4.72 (m, 1H), 4.24-4.05 (m, 2H), 3.67 (bs, 2H), 3.45 (t, J=6.3, 2H), 2.80 (t, J=12.6, 2H), 2.67-2.55 (m, 2H), 1.90-1.73 (m, 4H), 1.39 (s, 9H), 1.29-1.11 (m, 2H); MS (DCI+) m/z 636 (M+H)+.

후처리

  1. waitto proceed for 1 hour at ambient temperature
  2. extractionThe product was extracted with ethyl acetate
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 25%-75% ethyl acetate/hexanes, 0-15 minutes, 30 mL/minute)

출처 및 근거

ORD 기록
ord-74a7406a092f4c0aa25be85ca20e1bb9
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044069B2

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