Trimethyl orthoformate → HCID 9827593, compound

To the solution of N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (195 mg, 0.43 mmol) and N-Boc-3-pyrrolidone (91 mg, 0.49 mmol) in methanol (3 ml) was added trimethylorthoformate (2 ml) and three drops of acetic acid, at room temperature. This mixture was allowed to stir for 30 min. at room temperature and sodium cyanoborohydride (130 mg, 2.09 mmol) was added. Stirring was continued for a further 18 hours at room temperature and then the reaction mixture was concentrated. The residue was dissolved in ethylacetate (300 mL), and washed with saturated aqueous NaHCO3 and brine, then dried (Na2SO4) and evaporated. Purification of the residue by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2) gave the desired product (120 mg, 45%) as a mixture of diastereomers.

1. customat room temperature
2. stirringStirring
3. waitwas continued for a further 18 hours at room temperature
4. concentrationthe reaction mixture was concentrated
5. dissolutionThe residue was dissolved in ethylacetate (300 mL)
6. washwashed with saturated aqueous NaHCO3 and brine
7. dry with materialdried (Na2SO4)
8. customevaporated
9. customPurification of the residue by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2)

ORD record

ord-3fcb0949974c4e2c923c159c3f6d7f0e

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183273B2