Sodium Hydroxide → HCID 68452330, compound

HRID 272554Notes

Reaction equation

HRID 272554 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH2:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH2:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O)[CH3:17].[BH4-].[Na+].[OH-].[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][CH:21]1[CH2:22][CH2:23][N:18]([CH2:16][CH3:17])[CH2:19][CH2:20]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateHCID 123643854789-07-5

Product 1

HCID 68452330HCID 68452330, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.204 g (1 mmol) 5-amino-1H-indole-2-carboxylic acid ethyl ester, 133 mg (1 mmol) 1-ethyl piperidone and 0.35 ml (1 mmol) titanium(IV)isopropoxide in 1 ml methanol was treated after 3 h at room temperature with 0.023 g (1 mmol) sodium borohydride and the mixture was allowed to react during 16 h at room temperature. The mixture was poured on 50 ml ice/water and treated with 50 ml ethyl acetate and 5 ml 1 N NaOH aq. After 20 min the mixture was filtered through decalite and the aqueous phase was extracted with 50 ml ethyl acetate. The combined organic phases were washed with 50 ml NaCl sat., dried over Na2SO4 and after filtration evaporated to dryness. The residue was purified over silica eluting with a gradient of dichloromethane (DCM)/2N NH3 in methanol and 0.240 g (76%) of the title compound were isolated as brown solid. MS (m/e): 316.1 (MH+, 100%).

Workup

  1. customto react during 16 h at room temperature
  2. filtrationwas filtered through decalite
  3. extractionthe aqueous phase was extracted with 50 ml ethyl acetate
  4. washThe combined organic phases were washed with 50 ml NaCl sat.
  5. dry with materialdried over Na2SO4
  6. filtrationafter filtration
  7. customevaporated to dryness
  8. customThe residue was purified over silica eluting with a gradient of dichloromethane (DCM)/2N NH3 in methanol

Sources & evidence

ORD record
ord-86d65a8929044c65a1b30eec758d6811
Source dataset
uspto-grants-2008_11
Patent number
US07456174B2

Reaction notes

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