HCID 67923327, compound → HCID 54284405, compound

HRID 1084439Notes

Reaction equation

HRID 1084439 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](/[CH:18]=[CH:19]/[C@H:20]3[O:25][C:24](=[O:26])[CH2:23][C@H:22]([OH:27])[CH2:21]3)=[C:16]([CH:28]([CH3:30])[CH3:29])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:31])=[CH:4][CH:3]=1>ClCCl.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([CH2:18][CH2:19][C@H:20]3[O:25][C:24](=[O:26])[CH2:23][C@H:22]([OH:27])[CH2:21]3)=[C:16]([CH:28]([CH3:29])[CH3:30])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:31])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67923327HCID 67923327, compound

Product 1

HCID 54284405HCID 54284405, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (4R,6S)-(E)-6-[2-{2-(4-fluorophenyl)-4-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}ethen-1-yl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (0.6 g) in dichloromethane (20 ml) was hydrogenated at atmospheric pressure over 5% palladium on charcoal catalyst for 36 hours. The mixture was diluted with dichloromethane (100 ml) and filtered through diatomaceous earth to remove the catalyst. The filtrate was evaporated to give a gum. The gum was purified by flash chromatography (silica, ethyl acetate as eluent) to give a white solid which was recrystallised from a mixture of cyclohexane and dichloromethane to give (4R,6R)-6-[2-{2-(4-fluorophenyl)-4-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one as a white solid, m.p.192°-193° C. Found: C,70.7; H,6.15; N,3.24%. Required: C,70.9; H,6.15; N,3.31%. [NMR in CDCl3 /D2O, 1.20-1.88 (10H,m), 2.30-2.89 (4H,m), 3.46 (1H,sept,J=8 Hz), 4.26 (1H,m), 4.40 (1H,m), 7.24 (4H,m), 7.47 (1H,m), 7.69 (1H,m), 8.03 (1H,d,J=8 Hz), 8.44 (1H,m)].

Workup

  1. filtrationfiltered through diatomaceous earth
  2. customto remove the catalyst
  3. customThe filtrate was evaporated
  4. customto give a gum
  5. customThe gum was purified by flash chromatography (silica, ethyl acetate as eluent)
  6. customto give a white solid which
  7. customwas recrystallised from a mixture of cyclohexane and dichloromethane

Sources & evidence

ORD record
ord-9125f3e350e54d5ebfdad09c1c2fb6a1
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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