Furan-2-boronic acid → Methyl 4-(3-(furan-2-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601834Notes

Reaction equation

HRID 601834 reaction equation
C[C:2]1[C:3]2[C:22](=[O:23])CCC=2N(S(C2C=CC(C)=CC=2)(=O)=O)[C:6]=1C(O)=O.O=C1C2[CH:31]=[C:30]([C:33]([O:35][CH3:36])=O)NC=2CC1.BrC1C=C(C=CC=1)C[Mg]Br.Br[C:48]1[CH:49]=[C:50]([CH:74]=[CH:75][CH:76]=1)/[CH:51]=[C:52]1\[CH2:53][CH2:54][C:55]2[N:56]([S:64]([C:67]3[CH:73]=[CH:72][C:70]([CH3:71])=[CH:69][CH:68]=3)(=[O:66])=[O:65])[C:57]([C:60]([O:62][CH3:63])=[O:61])=[CH:58][C:59]\1=2.O1C=CC=C1B(O)O>>[O:23]1[CH:22]=[CH:3][CH:2]=[C:6]1[C:48]1[CH:49]=[C:50]([CH:74]=[CH:75][CH:76]=1)[CH2:51][CH:52]1[C:59]2[CH:58]=[C:57]([C:60]([O:62][CH3:63])=[O:61])[NH:56][C:55]=2[CH2:54][CH2:53]1.[O:35]1[CH:33]=[CH:30][CH:31]=[C:36]1[C:48]1[CH:49]=[C:50]([CH:74]=[CH:75][CH:76]=1)/[CH:51]=[C:52]1\[CH2:53][CH2:54][C:55]2[N:56]([S:64]([C:67]3[CH:68]=[CH:69][C:70]([CH3:71])=[CH:72][CH:73]=3)(=[O:66])=[O:65])[C:57]([C:60]([O:62][CH3:63])=[O:61])=[CH:58][C:59]\1=2

Participants

6

Reactant 4

HCID 2734357Furan-2-boronic acidHCID 66873689(E)-methyl 4-(3-bromobenzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 86638796Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (methyl 4-oxo-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate)HCID 178419662HCID 178419662, compound

Product 2

HCID 59180189Methyl 4-(3-(furan-2-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 66873562(E)-methyl 4-(3-(furan-2-yl)benzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Procedure

The title compound was synthesized in four steps. First, tosyl protected methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (methyl 4-oxo-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) (1.50 g, 8.37 mmol) was reacted with 3-bromobenzylmagnesium bromide (15 mL, 3.75 mmol) according to General Procedure 3 to give exo olefin-containing compound (E)-methyl 4-(3-bromobenzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by coupling with furan-2-boronic acid (0.138 g, 1.23 mmol) according to General Procedure 9.1 to give (E)-methyl 4-(3-(furan-2-yl)benzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, then tosyl deprotection according to General Procedure 10.1 to give (E)-methyl 4-(3-(furan-2-yl)benzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate. Hydrogenation of (E)-methyl 4-(3-(furan-2-yl)benzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate according to General Procedure 6, then purification by column (Isco CombiFlash) eluting with a gradient of 0-25% EtOAc/heptane afforded the title compound: 0.024 g.

Workup

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Sources & evidence

ORD record
ord-1b8cc35d720244ca8fa8fe19caae5dc3
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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