HCID 86744004, compound → HCID 23166601, compound

HRID 2107077Notes

Reaction equation

HRID 2107077 reaction equation
[OH:1][CH:2]([CH2:9][CH:10]([OH:35])/[CH:11]=[CH:12]/[C:13]1[C:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]2[C:25]=1[CH:26]([CH3:28])[CH3:27])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]>[O-2].[O-2].[Mn+4].C(OCC)C>[OH:1][CH:2]([CH2:9][C:10](=[O:35])/[CH:11]=[CH:12]/[C:13]1[C:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]2[C:25]=1[CH:26]([CH3:28])[CH3:27])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 86744004HCID 86744004, compound

Product 1

HCID 23166601HCID 23166601, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl (E)-3,5-dihydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)hept-6-enoate (157 mg; prepared as described in Example 3), activated manganese dioxide (1.74 g) and diethyl ether (25 ml) was stirred at the ambient temperature under an argon atmosphere for 2 hours. The suspension was then filtered and the solid was extracted with diethyl ether (3×15 ml). The filtrate was combined with the extracts and evaporated in vacuo, to give ethyl (E)-3-hydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]-isoquinolin-2-yl)-5-oxohept-6-enoate (80 mg), in the form of an orange gum. [N.M.R. (in CDCl3): 1.26 (3H, t, J=7 Hz), 1.55 (6H, d, J=7 Hz), 2.48 (2H, d, J=7 Hz), 2.55 (2H, d, J=7 Hz), 3.76 (1H, septet, J=7 Hz), 4.19 (2H, q, J=7 Hz), 4.41 (1H, quintet, J=7 Hz), 5.71 (1H, d, J=16 Hz), 6.73 (1H, d, J=8 Hz), 7.01-7.59 (9H, m), 7.03 (1H, d, J=8 Hz), 7.04 (1H, d, J=16 Hz); Mass spectrum (electron impact) m/e =469].

Workup

  1. filtrationThe suspension was then filtered
  2. extractionthe solid was extracted with diethyl ether (3×15 ml)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-5c5717fe5c134ec1901b4569c83887b1
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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