Methanol → HCID 13271044, compound

HRID 966514Notes

Reaction equation

HRID 966514 reaction equation
C(OC([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](/C=C/C(OC)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:26])=O)C1C=CC=CC=1.CO.[BH4-].[Li+].CCCCCC.[C:37](OCC)(=[O:39])[CH3:38]>C1COCC1>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[C:12]1[CH2:26][CH2:38][CH2:37][OH:39]

Participants

6

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 21226206Ethyl acetate hexaneHCID 23393875HCID 23393875, compound

Product 1

HCID 13271044HCID 13271044, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

5-((E)-2-Methoxycarbonyl-vinyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.200 g, 0.573 mmol, 1 eq) was suspended in dry THF (10 mL) under Ar. Methanol (0.116 mL, 2.87 mmol, 5.0 eq) was added followed by cooling to 4° C. and the addition of lithium borohydride (1.40 mL of 2 M, 2.87 mmol, 5.0 eq). The reaction mixture was stirred and allowed to warm to room temperature, then heated to reflux. The reaction was followed by TLC (CH2Cl2/MeOH 9/1). After 24 hours, the reaction was quenched with brine and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with CH2Cl2/MeOH 9/1. 0.149 g (81% yield) of the indole-propanol was obtained as a white solid, with some contamination by the E-allylic alcohol (20%-30%).

Workup

  1. temperatureto warm to room temperature
  2. temperatureheated to reflux
  3. customthe reaction was quenched with brine
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent
  8. customchromatographed
  9. washeluting with CH2Cl2/MeOH 9/1

Sources & evidence

ORD record
ord-e1afa2596c974e58909ff99a2e304c09
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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