Formaldehyde → 1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid
Reaction equation
[CH:1]1[CH:6]=[C:5]([OH:7])[CH:4]=[C:3]([CH2:8][C@H:9]([NH2:13])[C:10]([OH:12])=[O:11])[CH:2]=1.[CH2:14]=O>S(=O)(=O)(O)O>[OH:7][C:5]1[CH:4]=[C:3]2[C:2](=[CH:1][CH:6]=1)[CH2:14][NH:13][CH:9]([C:10]([OH:12])=[O:11])[CH2:8]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To 61.5 g of D, L-m-tyrosine suspended in 250 ml of 0.05N sulfuric acid aqueous solution, 48 ml of 37% formalin aqueous solution was added dropwise. The reaction mixture was stirred at 70° C. for 12 hours, and subjected to crystallization under ice cooling for 2 hours. The obtained crystal were filtered off, and dried at 60° C. under reduced pressure to obtain 65.6 g of Compound 1 (yield 100%). Compound 1 thus obtained was dissolved in an aqueous solution of 2N sodium hydroxide, and was then adjusted to pH 5 with concentrated hydrochloric acid. The precipitate was filtered off, washed with water and dried at 60° C. under reduced pressure to obtain 52.5 g of purified product of Compound 1.
Workup
- customsubjected to crystallization under ice cooling for 2 hours
- filtrationThe obtained crystal were filtered off
- customdried at 60° C. under reduced pressure
Sources & evidence
- ORD record
- ord-08da9000e23a474aa76346e5b6e961a9
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05602255
Reaction notes
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