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

HRID 1392731노트

반응식

HRID 1392731 반응식
[C@@H:1]1([NH2:7])[CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:6].[C:8]([O:12][C:13](ON=C(C1C=CC=CC=1)C#N)=[O:14])([CH3:11])([CH3:10])[CH3:9].O>C(Cl)Cl.C(N(CC)CC)C>[NH2:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[NH:7][C:13](=[O:14])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9]

참가 물질

6

반응물 3

HCID 962WaterHCID 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 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

(±)-trans-1,2-Cyclopentanediamine (WO98/30574) (692 mg) was dissolved in methylene chloride (10 ml), to which triethylamine (1.1 ml) and 2-(tert-butoxycarbonyloxy-imino)-2-phenylacetonitrile (493 mg) were added, and the mixture was stirred at 0° C. for 1 hour. Thereafter, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) were additionally added, and the mixture was stirred at room temperature for 7 hours. Water was added to the reaction mixture to separate an organic layer. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The residue was purified by flash column chromatography on silica gel (methylene chloride:methanol=9:1) to obtain the title compound (395 mg).

후처리

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 7 hours
  3. customto separate an organic layer
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by flash column chromatography on silica gel (methylene chloride:methanol=9:1)

출처 및 근거

ORD 기록
ord-d7b5c3f55cfc4acd874224a669e9dfb8
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342014B2

반응 노트

불러오는 중…