HCID 20316896, compound → HCID 12391016, compound

HRID 596258Notes

Reaction equation

HRID 596258 reaction equation
[BrH:1].[O:2]1[CH:7]=[CH:6][CH2:5][CH2:4][CH:3]1[CH2:8][NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:21])[C:16]=2[OH:20])[C:11]1=[O:22].[H][H]>[Pd].O>[BrH:1].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:21])[C:16]=2[OH:20])[CH:11]1[OH:22]

Participants

5

Reactant 2

HCID 20316896HCID 20316896, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12391016HCID 12391016, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In the presence of 2 parts of 5 % palladium-on-carbon, 2 parts of 2-(3,4-dihydro-2H-pyran-2-yl)methylamino-5,6-dihydroxy-3,4-dihydro-1(2H)-naphthalenone hydrobromide is catalytically reduced in 50 volume parts of water at ordinary temperature and pressure until no more hydrogen is absorbed. The catalyst is filtered off and the filtrate is freeze-dried. The above procedure yields 2 parts of 2-(tetrahydropyran-2-yl)methylamino-1,5,6-trihydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide as colorless crystals melting at 155°-158° C (decomposition). The product was identified as that of Example 5 by mixed melting point)

Workup

  1. customis absorbed
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is freeze-dried

Sources & evidence

ORD record
ord-c3a154c1720441208273ea5c9d22a848
Source dataset
uspto-grants-1977_03
Patent number
US04010202

Reaction notes

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