Acetone → HCID 68454739, compound

HRID 2354986Notes

Reaction equation

HRID 2354986 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]([NH:15][CH:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH3:21][C:22]([CH3:24])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.O.C(O)(=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:16]1[CH2:20][CH2:19][N:18]([CH:22]([CH3:24])[CH3:21])[CH2:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68454615HCID 68454615, compound

Product 1

HCID 68454739HCID 68454739, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.2 g (1 mmol) 5-(pyrrolidin-3-ylamino)-1H-indole-2-carboxylic acid ethyl ester, 0.042 g (1 mmol) acetone and 0.1 ml acetic acid in 10 ml THF was treated after 1 h with 0.233 g (1 mmol) sodium trisacetoxyborohydride at 0° C. The mixture was allowed to react for 39 h at room temperature. The mixture was treated with 5 ml water, 15 ml Na2CO3 aq. and 15 ml ethyl acetate and the aqueous phase was extracted with 40 ml ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified over silica eluting with a gradient formed from DCM/2N NH3 in methanol to yield 0.17 g (74%) of the title compound and light brown solid. MS (m/e): 316.3 (MH+, 100%).

Workup

  1. customto react for 39 h at room temperature
  2. extractionthe aqueous phase was extracted with 40 ml ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified over silica eluting with a gradient
  7. customformed from DCM/2N NH3 in methanol

Sources & evidence

ORD record
ord-d1693fc810734109b7fb116cfabfcda3
Source dataset
uspto-grants-2010_07
Patent number
US07754736B2

Reaction notes

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