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

HRID 546410ノート

反応式

HRID 546410 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>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]

参加物

6

反応物 3

HCID 962WaterHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2 回HCID 11412654cis-Cyclopentane-1,2-diamine

生成物 1

HCID 18442856rac-tert-butyl N-((1R,2S)-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

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.

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 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)

出典と根拠

ORDレコード
ord-f1b68db288d346b3aaf75f72f2383ae3
出典データセット
uspto-grants-2011_05
特許番号
US07935824B2

反応ノート

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