Triethylamine → 2-(3-Fluorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 1963273노트

반응식

HRID 1963273 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14]C)=[O:13])[CH2:9][CH2:8][N:7]1[C:16]([O:18][CH3:19])=[O:17].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9][CH2:8][N:7]1[C:16]([O:18][CH3:19])=[O:17]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734612Dimethyl 2-(3-fluorobenzyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 667325072-(3-Fluorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid수율 81%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

Dimethyl 2-(3-fluorobenzyl)piperidine-1,4-dicarboxylate (9.153 g, 29.59 mmol) was dissolved in acetonitrile (100 mL) and water (2 mL), then lithium bromide (20.56 g, 236.72 mmol) was added. Triethylamine (16.41 mL, 118.36 mmol) was added and the resulting brown suspension was heated at reflux for 2 h. Water (100 mL) and MTBE (300 mL) were added. The organic phase was extracted with water (×2). The pooled aqueous layer was acidified to pH 1 with 3.8 M HCl and then extracted with MTBE (×2). The combined organic layer was washed with water, dried over Na2SO4, filtered through a Celite containing filter and evaporated. 2-(3-Fluorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (7.07 g, 81%) was isolated as a yellow solid. MS m/z 296 (M+H)+

후처리

  1. temperaturethe resulting brown suspension was heated
  2. temperatureat reflux for 2 h
  3. extractionThe organic phase was extracted with water (×2)
  4. extractionextracted with MTBE (×2)
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through a Celite
  8. additioncontaining
  9. filtrationfilter
  10. customevaporated

출처 및 근거

ORD 기록
ord-17934ee07343465689d70a196658a3d5
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415378B2

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