Water → rac-tert-butyl N-((1R,2R)-2-aminocyclopentyl)carbamate

HRID 2104353노트

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HRID 2104353 반응식
[C@@H:1]1([NH2:7])[CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:6].C(N(CC)CC)C.[C:15]([O:19][C:20](ON=C(C1C=CC=CC=1)C#N)=[O:21])([CH3:18])([CH3:17])[CH3:16].O>C(Cl)Cl>[C:15]([O:19][C:20](=[O:21])[NH:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[NH2:7])([CH3:18])([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2회HCID 243938Cyclopentane-1,2-diamine

생성물 1

HCID 17040217rac-tert-butyl N-((1R,2R)-2-aminocyclopentyl)carbamate수율 98.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(±)-trans-1,2-Cyclopentanediamine (WO98/30574) (692 mg) was dissolved in methylene chloride (10 mL), and to the solution were added triethylamine (1.1 mL) and 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) at 0° C., followed by stirring at 0° C. for 1 hour. Subsequently, additional 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) was added thereto, and the thus-obtained mixture was stirred at room temperature for 7 hours. Water was added to the reaction mixture to partition the mixture. The organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The residue was purified by silica gel flash column chromatography (methylene chloride:methanol=9:1), to thereby give the title compound (395 mg).

후처리

  1. stirringthe thus-obtained mixture was stirred at room temperature for 7 hours
  2. customto partition the mixture
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate anhydrate
  5. customThe residue was purified by silica gel flash column chromatography (methylene chloride:methanol=9:1)

출처 및 근거

ORD 기록
ord-bebed518f25a460696381fb45085a585
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576135B2

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