Trimethylsilyldiazomethane → 2-tert-butyl 3-methyl (3S)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2,3-dicarboxylate

Temperature

0 °C

2-(t-Butyloxycarbonyl)-7-hydroxy-tetrahydro-isoquinoline-3-carboxylic acid (0.5 g, 1.71 mmol) was dissolved in 10% MeOH/CHCl3 (70 mL). The solution was cooled to 0° C. and trimethylsilyldiazomethane (2 M in hexane) (1.88 mL, 3.76 mmol) was added dropwise via syringe. A yellow color persisted after addittion of 1.2 mL of this reagent. The cooling bath was removed and the solution was stirred at 25° C. for 0.75 hr. The reaction was cooled to 0° C. and acetic acid was added dropwise until the yellow color disappeared. The solvent was evaporated in vacuo and the residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 solution (30 mL). The organic layer was washed with saturated NaCl solution (30 mL) and dried (MgSO4). Filtration and evaporation in the title compound which was used without further purification.

1. customThe cooling bath was removed
2. temperatureThe reaction was cooled to 0° C.
3. additionacetic acid was added dropwise until the yellow color
4. customThe solvent was evaporated in vacuo
5. customthe residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 solution (30 mL)
6. washThe organic layer was washed with saturated NaCl solution (30 mL)
7. dry with materialdried (MgSO4)
8. filtrationFiltration and evaporation in the title compound which
9. customwas used without further purification

ORD record

ord-6a7a60b90763425bb13617b15e1d406b

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05932590