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

HRID 390071

反応式

HRID 390071 の反応式
[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7]O)[CH2:4][O:3]1.[CH3:10][S:11]([O:14][CH2:15][C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1)(=[O:13])=[O:12].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC#N>[CH3:10][S:11]([O:14][CH2:15][C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1)(=[O:12])=[O:13].[CH2:23]([NH:30][CH2:7][C@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:9])[O:6]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 3

HCID 7504BenzylamineHCID 736057(+)-SolketalHCID 15570842HCID 15570842、化合物

生成物 2

HCID 11042283(S)-N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine収率 76%HCID 15570842HCID 15570842、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

(R)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate was prepared from (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (Sigma-Aldrich, 99% ee) by a known literature procedure (H. S. Kim, D. Barak, T. K. Harden, J. L. Boyer and K. A. Jacobson, J. Med. Chem., 2001, 44, 3092). 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.

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-2dafa71afaf54e4bb5b7cb2364c7cbdb
出典データセット
uspto-grants-2013_02
特許番号
US08383636B2

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