5-octyl-1H-indole → 5-Octylindoline

HRID 710288

Reaction equation

HRID 710288 reaction equation
[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>CC(O)=O.C(OCC)C>[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 1

HCID 667262575-octyl-1H-indole

Product 1

HCID 667265445-OctylindolineYield 62%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of the product of Step B (0.08 g; 0.35 mmol) in AcOH (1.5 ml) NaBH3CN was added at 0° C., with stirring. The resulting mixture was stirred for 2 h at room temperature, then diluted to 20 ml with diethyl ether and washed with 10% NaOH (2×5 ml), H2), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc; 9:1) to give the title compound (0.05 g; 62%) as a colourless syrup. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.54 (m, 2H); 2.48 (tr, 2H, J=7.9 Hz); 2.98 (tr, 2H, 9.2 Hz) 3.52 (tr, 2H, J=9.2 Hz); 6.56 (d, 1H, 7.8 Hz); 6.83 (d, 1H, J=7.8 Hz); 6.93 (s, 1H).

Workup

  1. stirringThe resulting mixture was stirred for 2 h at room temperature
  2. washwashed with 10% NaOH (2×5 ml), H2), brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe residue was purified by FCC (SiO2; hexane/EtOAc; 9:1)

Sources & evidence

ORD record
ord-3a8b52c5fd14417a8927cf8ac3da0858
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Linked notes

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