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Methyl chloroformate → Dimethyl 2-(3,5-difluorobenzyl)piperidine-1,4-dicarboxylate

HRID 1963319
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HRID 1963319 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][NH:7]1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][N:7]1[C:29]([O:30][CH3:31])=[O:32]
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참가 물질

5

반응물 3

HCID 6586Methyl chloroformate2회HCID 81531DiisopropylethylamineHCID 66731630Methyl 2-(3,5-difluorobenzyl)piperidine-4-carboxylate

생성물 1

HCID 66734958Dimethyl 2-(3,5-difluorobenzyl)piperidine-1,4-dicarboxylate수율 99.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methyl 2-(3,5-difluorobenzyl)piperidine-4-carboxylate (7.082 g, 26.30 mmol) was dissolved in DCM (170 mL) and DIPEA (5.50 mL, 31.56 mmol), then methyl carbonochloridate (2.88 mL, 36.58 mmol) was added. The reaction mixture was stirred at room temperature for 3 h, then additional methyl carbonochloridate (0.7 mL, 8.89 mmol) was added. The solution was stirred for 30 min then washed with 0.1 M HCl and satd NaHCO3. The organic phase was dried and concentrated to give dimethyl 2-(3,5-difluorobenzyl)piperidine-1,4-dicarboxylate (8.55 g, 99%). MS m/z 328 (M+H)+

후처리

  1. stirringThe solution was stirred for 30 min
  2. washthen washed with 0.1 M HCl
  3. customThe organic phase was dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-611e5d7d47c54d4c9cd864a83a2e034e
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415378B2

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