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Dichloromethane → HCID 69115646, 화합물

HRID 2054167
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HRID 2054167 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[C:15]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[C:16]([CH3:19])=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O1CCCC1>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])=[CH:14][C:15]=1[CH:20]1[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]1
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참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 60021094HCID 60021094, 화합물

생성물 1

HCID 69115646HCID 69115646, 화합물수율 77.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Benzyl chloroformate (95%, 4.52 mL, 30.1 mmol) was added dropwise to a stirred mixture of tert-butyl 4-(3-amino-6-methylphenyl)piperidinecarboxylate (6.99 g, 24.1 mmol) and K2CO3 (3.66 g, 26.4 mmol) in tetrahydrofuran (350 mL) and stirred under nitrogen for 18 h. CH2Cl2 was added to the reaction mixture, washed with NaHCO3 solution (saturated), followed by water, then dried over Na2SO4 and concentrated in vacuo to give an oil. Purification by flash column chromatography (eluent: cyclohexane:EtOAc (87:13)) gave tert-butyl 4-{2-methyl-5-[(phenylmethoxy)carbonylamino]phenyl}piperidinecarboxylate (7.90 g, 77.1% yield) as a white foam. ESMS m/e: 425.0 (M+H)+.

후처리

  1. washwashed with NaHCO3 solution (saturated)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. customPurification by flash column chromatography (eluent: cyclohexane:EtOAc (87:13))

출처 및 근거

ORD 기록
ord-9a05e85dae1841db8557fd041f0b83e3
출처 데이터셋
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07329656B2

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