tert-Butyl 6-hydroxy-8-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate synthesis
- Product Name:tert-Butyl 6-hydroxy-8-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
- CAS Number:1579518-38-9
- Molecular formula:C15H21NO3
- Molecular Weight:263.33
24424-99-5
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Yield:1579518-38-9 33.4 g
Reaction Conditions:
in dichloromethane at 15; for 12 h;
Steps:
25 Preparation of intermediate 6-Bromomethyl-8-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (25-14)
To this crude residue is added Boc2O (72 g, 0.33 mol) and triethylamine (63 g, 0.62 mol) and the resulting mixture is stirred for 12 h at 15° C., then diluted with dichloromethane (1500 mL) and water (100 mL).
The organics layer is washed with 0.5 N HCl (100 mL) and brine (100 mL), dried, concentrated, and purified by silica gel column (PE:EtOAc=30:1) to give 6-Hydroxy-8-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester, 25-10 (33.4 g) as a white solid.
References:
US2014/73629,2014,A1 Location in patent:Paragraph 0268
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