Benzylamine → HCID 57857600、化合物

HRID 17022ノート

反応式

HRID 17022 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:10][CH:9]1[CH:11]1[CH2:13][CH2:12]1.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(C)(C)C.[Na+].C(OCC)(=O)C>C(COC)OC>[CH2:14]([NH:21][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:10][CH:9]1[CH:11]1[CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 23676156Sodium t-butoxideHCID 673713862-(2-Chlorophenyl)bicyclopropyl

生成物 1

HCID 57857600HCID 57857600、化合物収率 87.1%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

3 g of 2-(2-chlorophenyl)bicyclopropyl (15.6 mmol, trans/cis ratio of about 2:1), 2.5 g of benzylamine (23.4 mmol), 2.4 g of sodium tert-butanolate (25 mmol), 35 mg of Pd(II) acetate (0.16 mmol) and 60 mg of R(−)-di-tert-butyl-[1-[(S)-2-(dicyclohexylphosphanyl)-ferrocenyl]ethyl]phosphine (0.11 mmol) are dissolved in 30 ml of dimethoxyethane. The reaction mixture is heated to the reflux temperature of the solvent and is stirred for 24 hours. After cooling, ethyl acetate is added and the organic phase is washed with water. The solvent is removed using a water jet vacuum and the residue is dried. The product is purified by column chromatography on silica gel (eluant:ethyl acetate/hexane 1:15). 3.58 g of benzyl(2-bicyclopropyl-2-yl-phenyl)amine (87% of theory) are obtained in the form of a brown oil (trans/cis ratio of about 2:1).

後処理

  1. temperatureThe reaction mixture is heated to the reflux temperature of the solvent
  2. temperatureAfter cooling
  3. washthe organic phase is washed with water
  4. customThe solvent is removed
  5. customthe residue is dried
  6. customThe product is purified by column chromatography on silica gel (eluant:ethyl acetate/hexane 1:15)

出典と根拠

ORDレコード
ord-02745a7007724ba18c99b68f891541fd
出典データセット
uspto-grants-2010_06
特許番号
US07737301B2

反応ノート

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