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

HRID 546410노트

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HRID 546410 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>ClCCl.C(N(CC)CC)C>[C:8]([O:12][C:13]([NH:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:1]1[NH2:7])=[O:14])([CH3:11])([CH3:10])[CH3:9]

참가 물질

6

반응물 3

HCID 962WaterHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2회HCID 11412654cis-Cyclopentane-1,2-diamine

생성물 1

HCID 18442856rac-tert-butyl N-((1R,2S)-2-aminocyclopentyl)carbamate수율 98.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

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온도
0 °C

실험 절차

cis-1,2-Cyclopentanediamine (WO98/30574) (692 mg) was dissolved in dichloromethane (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 saline and dried over anhydrous sodium sulfate. The residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=9:1) to obtain the title compound (395 mg) as a pale yellow oil.

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 saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=9:1)

출처 및 근거

ORD 기록
ord-f1b68db288d346b3aaf75f72f2383ae3
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935824B2

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