Sodium Iodide → 4-trimethylsilanyloxy-7,8-dihydro-6H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

HRID 982882Notes

Reaction equation

HRID 982882 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[CH2:6]([O:8][C:9]([C:11]1[C:12]2[C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][C:13]=2[N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:15]=1)=[O:10])[CH3:7].[Na+].[I-]>CC#N>[CH2:6]([O:8][C:9]([C:11]1[C:12]2[C:27]([O:28][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:26][CH2:25][CH2:24][CH2:23][C:13]=2[N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH:15]=1)=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 206056554-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Product 1

HCID 207622254-trimethylsilanyloxy-7,8-dihydro-6H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

TMSCl (4.03 ml, 31.74 mmol) is added slowly to a solution of 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (6.0 g, 18.67 mmol), NaI (4.76g, 31.74 mmol) and TEA (7.8 ml, 56 mmol ) in CH3CN (100 ml) at room temperature. The reaction mixture is stirred at room temperature for 18 h. It is then quenched with saturated NaHCO3 (aq., 70 ml). The layers are separated and the aqueous phase extracted with 1:1 EtOAC/hexanes. The organic layers are combined, dried (Na2SO4), and evaporated to afford the title compound as a brown oil . The title compound is used in the next step without further purification.

Workup

  1. customIt is then quenched with saturated NaHCO3 (aq., 70 ml)
  2. customThe layers are separated
  3. extractionthe aqueous phase extracted with 1:1 EtOAC/hexanes
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7b1fe30f4c4d442290189a46aa1d8f56
Source dataset
uspto-grants-2005_03
Patent number
US06861529B2

Reaction notes

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