Methanol → HCID 59370482, compound

To a solution of 5-methyl-6-(methyloxy)-3,4-dihydro-2(1H)-isoquinolinecarbaldehyde (Preparation 12; 1.49 g; 7.26 mmol) in dichloromethane (25 ml) at 0° C. under nitrogen was slowly added boron tribromide (9.09 g; 36.3 mmol). After 85 min at 0° C., methanol (25 ml) was added slowly, and the resulting mixture was left standing at room temperature for three days. Removal of the solvent and trituration with methanol/dichloromethane gave a white solid residue; the mother liquors were concentrated and the residue applied to an SCX solid phase extraction cartridge (20 g) and eluted with methanol followed by 2N ammonia in methanol to elute the product. After evaporation of the solvent the title compound (780 mg) was obtained as a pale yellow solid.

1. customat 0° C.
2. waitthe resulting mixture was left
3. waitstanding at room temperature for three days
4. customRemoval of the solvent and trituration with methanol/dichloromethane
5. customgave a white solid residue
6. concentrationthe mother liquors were concentrated
7. extractionthe residue applied to an SCX solid phase extraction cartridge (20 g)
8. washeluted with methanol
9. washto elute the product
10. customAfter evaporation of the solvent the title compound (780 mg)
11. customwas obtained as a pale yellow solid

ORD record

ord-94df4363ff25468f9d5dc592574f4787

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278324B2