Benzylamine → HCID 25223591、化合物

HRID 533185

反応式

HRID 533185 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.CCOC(C)=O.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CC#N.[O-][Mo]([O-])(=O)=O>[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

7

反応物 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 10236NinhydrinHCID 24903512[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate

生成物 1

HCID 25223591HCID 25223591、化合物収率 81.1%

試薬・触媒・溶媒 2

HCID 24621Molybdate ion触媒HCID 6342Acetonitrile溶媒

実験手順

The title compound was prepared in the same way as that method described for preparing the (S)-enantiomer (M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627). A solution of (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (3.0 g, 14.27 mmol) and benzylamine (6.23 ml, 57.1 mmol) were refluxed together in CH3CN (38 ml) for 48 h. Tlc (EtOAc-hex 8:2) showed a new product (uv/molybdate or ninhydrin) with Rf ˜0.3 together with a little higher running sm. 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 (R)—N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (2.56 g, 11.57 mmol, 81% yield) as a yellow oil. [α]D21 −3.7 (c, 0.885, CHCl3). 1H NMR (CDCl3, 300 MHz), δ ppm, 7.32-7.20 (m, 5H), 4.25, (m, 1H), 4.03 (dd, 1H, J 8.0, 6.4 Hz), 3.82 (s, 2H), 3.68 (dd, 1H, J 8.0, 6.8 Hz), 2.74 (d, 2H, J 5.7 Hz), 1.40 (s, 3H), 1.35 (s, 3H). 13C NMR (CDCl3, 75.5 MHz), δ ppm, 140.6, 128.8, 128.4, 127.3, 109.5, 75.8, 67.9, 54.4, 52.1, 27.3, 25.8.

後処理

  1. customThe title compound was prepared in the same way as that method
  2. customdescribed for preparing the (S)-enantiomer (M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627)
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with aqueous sat. NaHCO3
  6. customdried
  7. customthe solvent evaporated
  8. customThe residue was chromatographed (EtOAc-hex, 6:4

出典と根拠

ORDレコード
ord-b5504589053e4655a73fe4a91c83c464
出典データセット
uspto-grants-2014_10
特許番号
US08853224B2

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