Hydroquinone → 3-Bromo-2-methyl-3b,4,6,7,7a,8-hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester

HRID 30284Notes

Reaction equation

HRID 30284 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:14][CH:13]2[CH:9]([CH2:10][C:11]3[S:17][C:16]([CH3:18])=[CH:15][C:12]=32)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(Cl)(Cl)Cl.C1(C=CC(O)=CC=1)O.C1C(=O)N([Br:38])C(=O)C1>CC(O)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:14][CH:13]2[CH:9]([CH2:10][C:11]3[S:17][C:16]([CH3:18])=[C:15]([Br:38])[C:12]=32)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6212ChloroformHCID 67184N-bromobutanimideHCID 1317270432-Methyl-3b,4,6,7,7a,8-hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester

Product 1

HCID 1317270443-Bromo-2-methyl-3b,4,6,7,7a,8-hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product from step c) (411 mg, 1.55 mmol) in AcOH (3.8 ml) and CHCl3 (3.8 ml) was treated with hydroquinone (5 mg) and NBS (331 mg, 1.86 mmol) at 40° C. for 3 hours in the dark. Next, the reaction mixture was carefully quenched with sat. NaHCO3 (5 ml) and extracted with EtOAc (3×20 ml). The combined organic extracts were dried (MgSO4) and solvent evaporated in vacuo leaving the crude product that was purified by preparative TLC (hexanes:EtOAc-1:1) to give the subtitle compound. MS calculated for C14H18BrNO2S+H 344, observed 344, 346.

Workup

  1. customNext, the reaction mixture was carefully quenched with sat. NaHCO3 (5 ml)
  2. extractionextracted with EtOAc (3×20 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4) and solvent
  4. customevaporated in vacuo
  5. customleaving the crude product that
  6. customwas purified by preparative TLC (hexanes:EtOAc-1:1)

Sources & evidence

ORD record
ord-448b4fb992ea44399ed9fc9675d3b5c4
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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