Triethylamine → 2-(Cyclohexyloxymethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 1963245노트

반응식

HRID 1963245 반응식
[CH:1]1([O:7][CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][N:10]2[C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH:1]1([O:7][CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][CH2:11][N:10]2[C:19]([O:21][CH3:22])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 59536557Dimethyl 2-(cyclohexyloxymethyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 595365632-(Cyclohexyloxymethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid수율 100.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

Dimethyl 2-(cyclohexyloxymethyl)piperidine-1,4-dicarboxylate (2.54 g, 8.1 mmol) was dissolved in acetonitrile (35 mL) and water (0.7 mL), then lithium bromide (5.63 g, 64.80 mmol) was added. Triethylamine (4.49 mL, 32.40 mmol) was added and the resulting suspension was heated under reflux for 4 h. MTBE (100 mL) and water (50 mL) were added, the phases separated and the organic layer was extracted with water. The combined aqueous layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE. The combined organic layers were dried with Na2SO4 and evaporated. 2-(Cyclohexyloxymethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (2.43 g, quant.) was isolated. MS m/z 300 (M+H)+

후처리

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 4 h
  3. customthe phases separated
  4. extractionthe organic layer was extracted with water
  5. extractionextracted with MTBE
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-818cedaa229d45f0ac98f636de5b4c76
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415378B2

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