Diethylamine → 5-Methyl-2-oxo-cyclohexanecarboxylic acid diethylamide

HRID 1506715노트

반응식

HRID 1506715 반응식
C(O[C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5])C.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH2:14]([N:16]([CH2:17][CH3:18])[C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5])[CH3:15]

참가 물질

5

반응물 2

HCID 8021DiethylamineHCID 458119Ethyl 5-methyl-2-oxocyclohexane-1-carboxylate

생성물 1

HCID 666798285-Methyl-2-oxo-cyclohexanecarboxylic acid diethylamide수율 65.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매

실험 절차

5-Methyl-2-oxo-cyclohexanecarboxylic acid ethyl ester (45) (5.9 g, 32 mmol), DMAP (1.12 g, 10 mmol) and diethylamine (4.7 g, 65 mmol, 6.7 mL) in toluene (90 mL) were heated at reflux for 4 days. The reaction was allowed to cool and the toluene was removed under reduced pressure to give a yellow oil. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (20-50% B, 80 g) to afford 4.4 g (65%) of 5-methyl-2-oxo-cyclohexanecarboxylic acid diethylamide (46) as a yellow oil. The structure was confirmed 1H NMR (300 MHz, CDCl3) δH 0.8-1.05 (9H, m, CH3 and N(CH2CH3)2), 1.05-2.10 (5H, m, 5-CH and 4- and 6-CH2), 2.15-2.80 (2H, m, 3-CH2), 2.95-3.55 (5H, m, 1-CH and N(CH2CH3)2).

후처리

  1. temperatureat reflux for 4 days
  2. temperatureto cool
  3. customthe toluene was removed under reduced pressure
  4. customto give a yellow oil
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with petrol (A) and ethyl acetate (B) (20-50% B, 80 g)

출처 및 근거

ORD 기록
ord-a18cf294a02044b5872d086136027258
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09220795B2

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