Hydroxylamine → 2,3-Dihydro-1H-inden-1-one oxime
Reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH2:11][OH:12]>>[C:1]1(=[N:11][OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1Participants
Procedure
In Step 1 a 1-indanone is treated with a hydroxylamine and a base to produce a 1-indanone oxime. In Step 2 the oxime is hydrogenated to produce a corresponding primary amine, both R and S forms. In Step 3 the primary amine is then added to D-N-acetyl-3,4-dimethoxyphenylalanine in alcohol to produce the (R,R) and (R,S) salts of the primary amine. The (R,S) salt crystallizes first and the (R,R) salt is soluble. These are separated by filtration. The mother liquor, on concentrating and cooling precipitates the desired R,R isomer in high yield and optical purity. In Step 4 a solution of R,R isomer is treated with a base to produce the R form of the primary amine. In Step 5 the R primary amine is reacted with a tertiary amine and 6-chloropurineriboside to produce the adenosine compounds of Formula I of the present invention, for example, N6 -[1-(R)-indanyl]adenosine. ##STR4##
Sources & evidence
- ORD record
- ord-7063abc9928046d2b5b1ffa920002417
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04833273
Reaction notes
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