Triethylsilane → HCID 59180200, compound

HRID 601889Notes

Reaction equation

HRID 601889 reaction equation
[F:1][C:2]1([F:15])[CH2:13][C:5]2[NH:6][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:8][C:4]=2[C:3]1=O.C([SiH](CC)CC)C.CO.C(Cl)Cl>C(O)(C(F)(F)F)=O>[F:15][C:2]1([F:1])[CH2:13][C:5]2[NH:6][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:8][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 21226129Dichloromethane methanolHCID 59180149HCID 59180149, compound

Product 1

HCID 59180200HCID 59180200, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 5,5-difluoro-4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (111.2 mg, 0.517 mmol) in TFA (1 mL) under nitrogen at 25° C. was added triethylsilane (0.25 mL, 1.55 mmol) and the reaction mixture was stirred for 18 h at 25° C. TLC analysis (10% MeOH/DCM) indicated that all starting material had been consumed. The solvent was removed using a nitrogen stream and the residue was taken up in MeCN and purified by reverse-phase chromatography (MeCN/H2O, 0.05% TFA) to afford 3.9 mg of methyl 5,5-difluoro-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate in 3.8% yield. 1H NMR (400 MHz, ACETONE-d6) δ ppm 3.15 (t, 2H), 3.31 (t, 2H), 3.76 (s, 3H), 6.64 (d, 1H), 10.83 (bs, 1H); 19F NMR (400 MHz, Acetone-d6) δ ppm −86.73; LCMS-MS (ESI+) 202.0 (M+H).

Workup

  1. customhad been consumed
  2. customThe solvent was removed
  3. custompurified by reverse-phase chromatography (MeCN/H2O, 0.05% TFA)

Sources & evidence

ORD record
ord-22f91b9cc62c49569f8c59fe24c7d7e1
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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