Benzylamine → HCID 25223591, compound

HRID 533185

Reaction equation

HRID 533185 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 25223591HCID 25223591, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 24621Molybdate ionCatalystHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b5504589053e4655a73fe4a91c83c464
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Linked notes

Loading…