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

HRID 1392731ノート

反応式

HRID 1392731 の反応式
[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]

参加物

6

反応物 3

HCID 962WaterHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2 回HCID 243938Cyclopentane-1,2-diamine

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

(±)-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).

後処理

  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)

出典と根拠

ORDレコード
ord-d7b5c3f55cfc4acd874224a669e9dfb8
出典データセット
uspto-grants-2008_03
特許番号
US07342014B2

反応ノート

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