HCID 86744702, compound → HCID 86744701, compound

HRID 1084435Notes

Reaction equation

HRID 1084435 reaction equation
[OH:1][C@H:2]([CH2:8][C@H:9]([OH:33])/[CH:10]=[CH:11]/[C:12]1[N:13]([CH:30]([CH3:32])[CH3:31])[C:14](=[O:29])[C:15]2[C:20]([C:21]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:3][C:4]([O:6][CH3:7])=[O:5]>ClCCl.[O-2].[O-2].[Mn+4]>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:29])[N:13]([CH:30]([CH3:32])[CH3:31])[C:12]=2/[CH:11]=[CH:10]/[C:9](=[O:33])[CH2:8][C@@H:2]([OH:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5])=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 86744702HCID 86744702, compound

Product 1

HCID 86744701HCID 86744701, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl (3R,5S)-(E)-3,5-dihydroxy-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]hept-6-enoate (as prepared in Example 10; 1.6 g) in dichloromethane (160 ml) was stirred at room temperature under argon with the exclusion of light. Manganese dioxide was added portionwise (4×4 g) over 3 hours and the mixture stirred for a further 17 hours. The mixture was filtered through diatomaceous earth and the filter pad washed with dichloromethane (3×50 ml). The combined filtrate and washings were evaporated to give a viscous orange gum which was purified by flash chromatography on silica gel using diethyl ether as eluant to give methyl (3R)-(E)-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]-3-hydroxy-5-oxohept-6-enoate as a yellow foam (NMR (in CDCl3): 1.70 (6H, d, J=8 Hz), 2.47 (2H, d, J=6 Hz), 2.58 (2H, m), 3.30 (1H, d, J=4 Hz), 3.76 (3H, s), 4.28-4.58 (2H, m plus sept), 5.99 (1H, d, J=16 Hz), 6.97-7.59 (8H, m), 8.43 (1H, m)].

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter pad washed with dichloromethane (3×50 ml)
  3. customThe combined filtrate and washings were evaporated
  4. customto give a viscous orange gum which
  5. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-91c4b555858d4c6aabd8812fd26d797e
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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