Water → Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

HRID 1500518노트

반응식

HRID 1500518 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClC(Cl)C.C(O)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:27]2[CH2:28][CH2:29][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH2:25][CH2:26]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 643495Benzyl piperazine-1-carboxylateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 18971584Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate수율 74%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 63651,1-Dichloroethane용매

실험 절차

A mixture of piperazine-1-carboxylic acid benzyl ester (6.6 g, 29.96 mmol) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester in dichloroethane (150 mL) containing two drops of acetic acid was stirred at RT for 1 h and then sodium triacetoxyborohydride (19.05 g, 89.89 mmol) was added in portions. The reaction mixture was stirred at RT overnight, water (150 mL) was added, and the reaction mixture was stirred at RT for 2 h. The reaction mixture was extracted with DCM (4×30 mL). Combined organic layers were dried over sodium sulfate, filtered, concentrated under reduced pressure, and purified by silica gel chromatography (20-30% EtOAc/petroleum ether) to provide the title intermediate (9 g, 74% yield) as a colorless oil. (m/z): [M+H]+ calcd for C22H33N3O4 404.25, found 404.3.

후처리

  1. stirringThe reaction mixture was stirred at RT overnight
  2. stirringthe reaction mixture was stirred at RT for 2 h
  3. extractionThe reaction mixture was extracted with DCM (4×30 mL)
  4. dry with materialCombined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography (20-30% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-2678d2562eff463aab5d83ef934c8f86
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206159B2

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