Water → HCID 16660039, compound

HRID 2264689Notes

Reaction equation

HRID 2264689 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:17][CH:16]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[N:25]1([CH2:24][CH2:23][CH2:22][O:21][C:18]2[CH:17]=[CH:16][C:15]([N:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:14]=[C:6]3[CH2:4][OH:3])=[CH:20][CH:19]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 16660038HCID 16660038, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 16660039HCID 16660039, compoundYield 0.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

(1-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-1H-indole-2-carboxylic acid ethyl ester (0.5 g, 1.27 mmol) was dissolved in THF (10 mL) and added dropwise to lithium aluminum hydride (1.53 mL, 1 M solution in THF, 1.53 mmol) in THF (10 mL). The reaction was stirred at 60° C. for 2 hours. Water (0.3 mL), 2 N NaOH (0.3 mL), and water (0.9 mL) were added, and the solvent was evaporated. The resulting residue was diluted with water and extracted with dichloromethane. The dichloromethane extracts were dried over MgSO4 and concentrated to give a white solid, 0.36 g. A small amount of the product was purified by semi-prep LC-MS to give 3.5 mg of pure desired product. LC-MS (C22H26N2O2 calc'd 350) m/z 351 (M+H); 1H NMR (300 MHz, CDCl3) d 7.65-7.61 (m, 1H), 7.35 (d, J=8.7 Hz, 2H), 7.16-7.08 (m, 3H), 7.01 (d, J=8.7 Hz, 2H), 6.65 (s, 1H), 4.64 (s, 2H), 4.10 (t, J=6 Hz, 2H), 2.93-2.86 (m, 6H), 2.21-2.12 (m, 2H), 1.94-1.90 (m, 4H).

Workup

  1. customthe solvent was evaporated
  2. additionThe resulting residue was diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe dichloromethane extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customto give a white solid, 0.36 g
  7. customA small amount of the product was purified by semi-prep LC-MS

Sources & evidence

ORD record
ord-ae23caff4ae049fd95b2c37ad15ded5f
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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