Hydrogen Peroxide → 1-benzyl-1H-indole-3-carbaldehyde O-(3-hydroxy-propyl)-oxime

HRID 1392264Notes

Reaction equation

HRID 1392264 reaction equation
[CH2:1]([O:4][N:5]=[CH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]=1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH:32]O.[OH-].[Na+]>O1CCCC1>[OH:32][CH2:3][CH2:2][CH2:1][O:4][N:5]=[CH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86040275HCID 86040275, compound

Product 1

HCID 865983641-benzyl-1H-indole-3-carbaldehyde O-(3-hydroxy-propyl)-oximeYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-benzyl-1H-indole-3-carbaldehyde O-allyl-oxime (2.965 g, 10.2 mmol) in tetrahydrofuran (50 mL) cooled to 0° C. was added 9-BBN (0.5 M in THF)(50.0 mL, 25.0 mmol). The reaction was stirred at 0° C. for 1 hour and then warmed to room temperature over 30 minutes. Hydrogen peroxide (12 mL) was carefully added followed by a 10% NaOH solution (20 mL) and stirring continued at room temperature for 25 minutes. The reaction was quenched by the addition of saturated sodium bisulfite and extracted with ethyl acetate. The combined organic were washed with saturated sodium bisulfite and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography through silica gel using ethyl acetate/hexanes (10/90 to 40/60) to give 1-benzyl-1H-indole-3-carbaldehyde O-(3-hydroxy-propyl)-oxime (1.298 g, 41%) as a white solid. mp=76.4-77.7° C.; mass spectrum (+ES, M+H) m/z 309. 1H NMR (400 MHz, CDCl3); δ 8.33 (s, 1H), 8.01 (d, 1H), 7.92 (s, 1H), 7.49 (d, 1H), 7.22 (m, 7H), 5.44 (s, 2H), 4.47 (t, 1H), 4.13 (t, 2H), 3.52 (q, 2H), 1.82 (m, 2H). Elemental analysis: Calcd. for C19H20N2O2: C, 74.0; H, 6.54; N, 9.08. Found: C, 73.74; H, 6.46; N, 8.95.

Workup

  1. temperaturewarmed to room temperature over 30 minutes
  2. stirringstirring
  3. waitcontinued at room temperature for 25 minutes
  4. customThe reaction was quenched by the addition of saturated sodium bisulfite
  5. extractionextracted with ethyl acetate
  6. washThe combined organic were washed with saturated sodium bisulfite and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-150175bc4ccc4f7ba02a94d42c367ecd
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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