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

HRID 2104353ノート

反応式

HRID 2104353 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 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 1

HCID 6344Dichloromethane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), 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).

後処理

  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)

出典と根拠

ORDレコード
ord-bebed518f25a460696381fb45085a585
出典データセット
uspto-grants-2009_08
特許番号
US07576135B2

反応ノート

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