Sodium Hydroxide → 1-(4-ethylbenzyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine

HRID 2187817

반응식

HRID 2187817 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][C:20]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:30]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)[CH3:31].[BH3-]C#N.[Na+].[OH-].[Na+]>CC(O)=O.CO.ClCCl>[CH2:30]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36][N:27]2[CH2:28][CH2:29][CH:24]([CH2:23][NH:22][C:20](=[O:21])[CH2:19][NH:18][C:16]([O:15][CH2:14][CH:12]3[C:13]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)=[O:17])[CH2:25][CH2:26]2)=[CH:34][CH:33]=1)[CH3:31]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 208614-EthylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 543594714-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine

생성물 1

HCID 692145361-(4-ethylbenzyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine수율 62.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 10129899Acetic acid methanol용매

반응 조건

온도
60 °C

실험 절차

To A solution of 4-[{N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]piperidine (1.00 g, 2.33 mmol) in 2.5% AcOH/CH3OH (80 mL) were added 4-ethylbenzaldehyde (1.09 g, 8.16 mmol) and NaBH3CN (6.59 g, 10.5 mmol). The reaction mixture was stirred at 60° C. for 13 h. After the mixture was cooled to room temperature, 1 N aqueous NaOH solution (50 mL) and dichloromethane (50 mL) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (SiO2, CH3OH/AcOEt 2:8) afforded 1-(4-ethylbenzyl)-4-[{N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]piperidine (740 mg, 62%).

후처리

  1. temperatureAfter the mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (50 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cc844c6e573849f6936b3540a4bea5ee
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06410566B1

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