Carbon Dioxide → HCID 59495804, 화합물

HRID 400749

반응식

HRID 400749 반응식
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH3:19])=[C:9]([CH2:20][O:21][CH3:22])[CH:8]=1.[C:23](=[O:25])=[O:24]>CCOCC.CCOCC.CCOC(C)=O.O>[CH3:22][O:21][CH2:20][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19])[C:23]([OH:25])=[O:24]

참가 물질

7

반응물 3

HCID 280Carbon DioxideHCID 585541231-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidineHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 59495804HCID 59495804, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 21584169Diethylether ethylacetate용매

실험 절차

To anhydrous Et2O (130 mL) at −78° C. was added tert-butyllithium (63.79 mL; 1.50 M; 95.68 mmol) (solution in pentane) which was followed by the slow addition of a solution of 1-[4-bromo-2-(methoxymethyl)phenyl]-2-methylpiperidine obtained in step 3 (12.97 g; 43.49 mmol) in anhydrous Et2O (20 mL). After 40 min, the reaction mixture was poured on an excess of freshly crushed dry ice and stirred for 30 min after which time it was diluted with Et2O/EtOAc (1:1), water (pH 4-5). The organic layers were combined, dried over MgSO4 and the solvents were removed under reduced pressure to give a yellow oil that was triturated in iPr2O and pentane, filtered off and washed with pentane to give the title compound as a beige powder. 1H NMR (CDCl3, 300 MHz) δ 8.22 (d, J=2.1 Hz, 1H), 8.00 (dd, J=8.3, 2.1 Hz, 1H), 7.17 (d, J=8.3 Hz, 1H), 4.60 (d, J=12.3 Hz, 1H), 4.55 (d, J=12.3 Hz, 1H), 3.46 (s, 3H), 3.17 (m, 1H), 3.02 (m, 1H), 2.63 (m, 1H), 1.88-1.65 (m, 4H), 1.55-1.40 (m, 2H), 0.88 (d, J=6.2 Hz, 3H). LC/MS (Method B): 264.1 (M+H)+.

후처리

  1. dry with materialdried over MgSO4
  2. customthe solvents were removed under reduced pressure
  3. customto give a yellow oil that
  4. customwas triturated in iPr2O
  5. filtrationpentane, filtered off
  6. washwashed with pentane

출처 및 근거

ORD 기록
ord-ae1ead1750264a5592ce7d31955bbf06
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741923B2

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