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

HRID 390071

Reaction equation

HRID 390071 reaction equation
[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

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 736057(+)-SolketalHCID 15570842HCID 15570842, compound

Product 2

HCID 11042283(S)-N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamineYield 76%HCID 15570842HCID 15570842, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-2dafa71afaf54e4bb5b7cb2364c7cbdb
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Linked notes

Loading…