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

HRID 497397Notes

Reaction equation

HRID 497397 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][C:8]=2[N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:10]=1)=[O:5])[CH3:2].[I-].[Na+].C(N(CC)CC)C.[CH3:33][Si:34](Cl)([CH3:36])[CH3:35]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22]([O:23][Si:34]([CH3:36])([CH3:35])[CH3:33])=[CH:21][CH2:20][CH2:19][CH2:18][C:8]=2[N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 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 esterYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (4.6 mmol), sodium iodide (9.3 mmol), and triethylamine (13.9 mmol) in 15 mL acetonitrile is added trimethylsilyl chloride (9.3 mmol). After stirring at RT for 2 hours it is quenched with 20 mL saturated NaHCO3 solution and extracted several times with EtOAc. The combined organic layers are dried over Na2SO4 and evaporated in vacuo yielding 4-trimethylsilanyloxy-7,8-dihydro-6H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester as a brown oil (95%). 1H NMR (CDCl3) 0.15 (s, 9H), 1.32 (t, 3H), 1.60 (s, 9H), 1.83-1.97 (m, 2H), 1.99-2.06 (m, 2H), 3.00 (t, 2H), 4.33 (q, 2H), 5.40 (t, 1H), 7.62 (s, 1H). Step 2:

Workup

  1. customis quenched with 20 mL saturated NaHCO3 solution
  2. extractionextracted several times with EtOAc
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-58dd2cd7c12a4a329e8ea0455bd4768d
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

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