(-)-(R)-N-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl) methyl-N-phenylmethyl-N'-(2-pyrimidinyl)-1,2-ethanediamine → (-)-(R)-N-[(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamine

HRID 55374Notes

Reaction equation

HRID 55374 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@H:9]([CH2:11][N:12](CC3C=CC=CC=3)[CH2:13][CH2:14][NH:15][C:16]3[N:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:8][CH2:7][C:6]=2[CH:29]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@H:9]([CH2:11][NH:12][CH2:13][CH2:14][NH:15][C:16]3[N:17]=[CH:18][CH:19]=[CH:20][N:21]=3)[CH2:8][CH2:7][C:6]=2[CH:29]=1

Participants

5

Reactant 2

HCID 54139397(-)-(R)-N-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl) methyl-N-phenylmethyl-N'-(2-pyrimidinyl)-1,2-ethanediamineHCID 178418361HCID 178418361, compound

Product 1

HCID 54225259(-)-(R)-N-[(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamineYield 55.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8.4 g of (-)-(R)-N-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl) methyl-N-phenylmethyl-N'-(2-pyrimidinyl)-1,2-ethanediamine and 150 ml methanol was hydrogenated in the presence of 2 g of palladium-on-charcoal catalyst (10%). After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 90:10). The eluent of the desired fraction was evaporated and the residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.5 g (55.1%) of (-)-(R)-N-[(6-fluoro-3,4-dihydro-2H-1-benzopyran-2yl)methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamine; mp. 103.2° C. [α]D 20 =-76.58° (conc.=1% in CH3OH) (comp. 46).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 90:10)
  4. customThe eluent of the desired fraction was evaporated
  5. customthe residue was crystallized from 2,2'-oxybispropane
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-c0a9cd3f37df45aab5db38bdb7392bb6
Source dataset
uspto-grants-1997_04
Patent number
US05624952

Reaction notes

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