Trifluoroacetic acid → trans-[2-(3-Ethyl-pyrrol-1-yl)-cydohexyl]-carbamic acid tert-butyl ester

HRID 2218561Notes

Reaction equation

HRID 2218561 reaction equation
C[Mg]Cl.[C:4]([O:8][C:9](=[O:24])[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[N:17]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18]1)([CH3:7])([CH3:6])[CH3:5].[CH2:25]([SiH](CC)CC)C.FC(F)(F)C(O)=O>O1CCCC1>[C:4]([O:8][C:9](=[O:24])[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[N:17]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:25])=[CH:18]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86605566trans-[2-(3-Formyl-pyrrol-1-yl)-cyclohexyl]-carbamic acid tert-butyl esterHCID 178418332HCID 178418332, compound

Product 1

HCID 68976706trans-[2-(3-Ethyl-pyrrol-1-yl)-cydohexyl]-carbamic acid tert-butyl esterYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium chloride solution (3 M in tetrahydrofuran, 0.23 ml, 0.68 mmol) was added at −78° C. to a solution of trans-[2-(3-formyl-pyrrol-1-yl)-cyclohexyl]-carbamic acid tert-butyl ester (example 26a, 100 mg, 0.34 mmol) in tetrahydrofuran (2 ml), then after 3.5 h the reaction was quenched by addition of saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic layer was washed with brine, dried (MgSO4), and evaporated. This crude material (103 mg) was dissolved in dichloromethane (2 ml) and treated with triethylsilane (58 mg, 0.50 mmol) and trifluoroacetic acid (190 mg, 1.67 mmol). The reaction mixture was allowed to reach 0° C. over 3 h, then evaporated and the residue chromatographed (SiO2, heptane-ethyl acetate gradient) to afford the title compound (27 mg, 28%). Yellow solid, MS (ISP) 293.2 (M+H)+.

Workup

  1. customafter 3.5 h the reaction was quenched by addition of saturated aqueous ammonium chloride solution
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThis crude material (103 mg) was dissolved in dichloromethane (2 ml)
  7. customevaporated
  8. customthe residue chromatographed (SiO2, heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-5aad20c519dc4e88a7e8488ed73bfce9
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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