Triethylamine → HCID 66732104, 화합물

HRID 1963312노트

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HRID 1963312 반응식
[F:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([O:13]C)=[O:12])[CH2:8][CH2:7][N:6]1[C:15]([O:17][CH3:18])=[O:16].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[F:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8][CH2:7][N:6]1[C:15]([O:17][CH3:18])=[O:16]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734456Dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 66732104HCID 66732104, 화합물수율 96%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

To a solution of dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylate (8.08 g, 24.69 mmol) in acetonitrile (85 mL) and water (1.7 mL) was added lithium bromide (4.95 mL, 197.48 mmol) and triethylamine (13.69 mL, 98.74 mmol). The reaction mixture was heated to reflux for 2.5 h, then allowed to cool to room temperature. Water (150 mL) and MTBE (300 mL) was added. The aqueous phase was separated and the organic phase was extracted twice with water. The water phases were combined and 4.0 M HCl was added until a pH of 1 was obtained. The aqueous was extracted with MTBE (300 mL×2). The organic phases were combined, washed with brine, dried with Na2SO4 and evaporated under reduced pressure to give 2-(2,5-difluorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (7.4 g, 96%). MS m/z 314 (M+H)+

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2.5 h
  3. customThe aqueous phase was separated
  4. extractionthe organic phase was extracted twice with water
  5. addition4.0 M HCl was added until a pH of 1
  6. customwas obtained
  7. extractionThe aqueous was extracted with MTBE (300 mL×2)
  8. washwashed with brine
  9. dry with materialdried with Na2SO4
  10. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-646a8fb5c1cb4d8da110a5b14e4f6acc
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415378B2

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