Cyclohexene → 3-Cyclohex-2-enyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

HRID 852557Notes

Reaction equation

HRID 852557 reaction equation
COC(=O)C1C=C(N2CCCC2=O)C=C(Br)C=1.C1CCCCC=1.[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[C:31]([N:33]2[CH2:37][CH2:36][CH2:35][C:34]2=[O:38])[CH:30]=[C:29]([CH:39]2[CH2:44][CH2:43][CH:42]=[CH:41][CH2:40]2)[CH:28]=1.COC(=O)C1C=C(N2CCCC2=O)C=C(C2CCCCC=2)C=1>>[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[C:31]([N:33]2[CH2:37][CH2:36][CH2:35][C:34]2=[O:38])[CH:30]=[C:29]([CH:39]2[CH2:44][CH2:43][CH2:42][CH:41]=[CH:40]2)[CH:28]=1

Participants

5

Reactant 4

HCID 8079CyclohexeneHCID 22253055Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoateHCID 693568733-Cyclohex-1-enyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl esterHCID 69357337HCID 69357337, compound

Product 1

HCID 693596123-Cyclohex-2-enyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl esterYield 30%

Procedure

Description 74 was prepared in an analogous manner to that described for Description 73 from 686 mg (mmol) of 3-bromo-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D9a) and cyclohexene which yielded 207 mg (30%) of 3-cyclohex-2-enyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester, 3-cyclohex-3-enyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester and 3-cyclohex-1-enyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D74) after purification by flash chromatography on silica gel (iso-hexane/EtOAc: 5/1)

Workup

  1. customDescription 74 was prepared in an analogous manner to that

Sources & evidence

ORD record
ord-9d6b821dff154933bb275a6851b42c9d
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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