Benzylamine → (S)-N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine

HRID 533191ノート

反応式

HRID 533191 の反応式
CS(O[CH2:6][C@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8]1)(=O)=O.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC#N>[CH2:14]([NH:21][CH2:6][C@H:7]1[CH2:11][O:10][C:9]([CH3:12])([CH3:13])[O:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 7504BenzylamineHCID 15570842Methanesulfonic acid [(R)-2,2-dimethyl-[1,3]dioxolan-4-yl]methyl ester

生成物 1

HCID 11042283(S)-N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine収率 76%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

The title compound was prepared in the same way as described by M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627. A solution of (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (3.9 g, 18.55 mmol) and benzylamine (8.10 ml, 74.2 mmol) was refluxed in CH3CN (50 ml) for 48 h. The solvent was evaporated and the residue dissolved in EtOAc and washed with aqueous sat. NaHCO3, dried and the solvent evaporated. The residue was chromatographed (EtOAc-hex, 6:4 then 8:2) to give (S)—N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (3.1 g, 14.01 mmol, 76% yield) as a yellow oil. [α]D21 +4.3 (c, 0.69, CHCl3). The 1H NMR and 13C NMR were identical to that of compound 3.2.

後処理

  1. customThe title compound was prepared in the same way
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in EtOAc
  4. washwashed with aqueous sat. NaHCO3
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was chromatographed (EtOAc-hex, 6:4

出典と根拠

ORDレコード
ord-0b8544a54aa94a45922017aa49d330a9
出典データセット
uspto-grants-2014_10
特許番号
US08853224B2

反応ノート

読み込み中…