Carbon Dioxide → HCID 59495804、化合物

HRID 2410477

反応式

HRID 2410477 の反応式
C([Li])(C)(C)C.CCCCC.Br[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]2[CH3:24])=[C:14]([CH2:25][O:26][CH3:27])[CH:13]=1.[C:28](=[O:30])=[O:29]>CCOCC.CCOCC.CCOC(C)=O>[CH3:27][O:26][CH2:25][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH3:24])[C:28]([OH:30])=[O:29]

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 8003PentaneHCID 585541231-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 59495804HCID 59495804、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 21584169Diethylether ethylacetate溶媒

反応条件

温度
-78 °C

実験手順

A 1.5M solution of tert-butyllithium in pentane (64 mL, 95 mmol) was added into anhydrous Et2O (130 mL) cooled at −78° C. A solution of 1-[4-bromo-2-(methoxymethyl)phenyl]-2-methylpiperidine (13.0 g, 43.5 mmol) in anhydrous Et2O (20 mL) was added slowly. After 40 minutes, the reaction mixture was poured on an excess of freshly crushed dry ice and stirred for 30 min. The mixture was diluted with Et2O/EtOAc (1:1, 800 mL) and washed with water (200 mL, pH=4-5 adjusted with a 5N aqueous solution of HCl). The aqueous layer was extracted with EtOAc (400 mL). The organic layers were combined, dried (MgSO4) and the solvents were removed under reduced pressure to give a yellow oil, which was triturated in iPr2O (˜20 mL) and pentane (˜20 mL). The precipitate was filtered off, washed with pentane and dried under reduced pressure to give the title compound as a beige powder. HPLC (Method A), Rt: 1.6 min (purity: 93.5%). HPLC/MS, M+(ESI): 264.2, M−(ESI): 262.2. 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).

後処理

  1. washwashed with water (200 mL, pH=4-5
  2. extractionThe aqueous layer was extracted with EtOAc (400 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvents were removed under reduced pressure
  5. customto give a yellow oil, which
  6. customwas triturated in iPr2O (˜20 mL)
  7. filtrationThe precipitate was filtered off
  8. washwashed with pentane
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-28e16b203b4d41e895c700bb74d67b6b
出典データセット
uspto-grants-2014_08
特許番号
US08815919B2

関連ノート

読み込み中…