Piperidine → Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate

HRID 1183807Notes

Reaction equation

HRID 1183807 reaction equation
[CH:1]1[C:5]2=[C:6]3[C:10]([CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:8]=[CH:7]3.N1CCCCC1>CN(C=O)C>[CH2:7]1[C:6]2=[C:5]3[C:4](=[CH:12][CH:11]=[C:10]2[NH:9][CH2:8]1)[NH:3][C:2]([C:13]([O:15][CH3:16])=[O:14])=[CH:1]3

Participants

4

Reactant 2

HCID 8082PiperidineHCID 178496869HCID 178496869, compound

Product 1

HCID 15480266Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylateYield 370%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3 (15 mg, 0.014 mmol) in DMF (2 mL) was treated with 5% piperidine in DMF (2 mL). The reaction mixture was stirred for 5 min at 25° C. The final product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column), eluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient: 10% acetonitrile in 5 min, 10% to 50% acetonitrile in 15 min, maintaining 50% acetonitrile in 5 min, 50% to 100% acetonitrile in 5 min, to obtain 4 (11.2 mg, 95%). MS: calcd for C44H48ClN7O7 (M+H) m/z 822.33 found 822.6.

Workup

  1. customThe final product was purified by Prep HPLC (SymmetrPrep C18, 7 μm, 19×150 mm column)
  2. washeluted at 10 ml/min (0.01% TFA in water/acetonitrile) with a gradient
  3. wait10% acetonitrile in 5 min
  4. wait10% to 50% acetonitrile in 15 min
  5. temperaturemaintaining 50% acetonitrile in 5 min
  6. wait50% to 100% acetonitrile in 5 min

Sources & evidence

ORD record
ord-0bd985f3e30c412098d444ab83d38ea9
Source dataset
uspto-grants-2014_03
Patent number
US08664407B2

Reaction notes

Loading…