Sodium Methoxide → HCID 18398756, compound

HRID 1018916Notes

Reaction equation

HRID 1018916 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:9]1[Br:26])=O)(C)(C)C.C[O-].[Na+]>CO>[Br:26][C:9]1[NH:8][C:16]2[C:11]([C:10]=1[CH2:17][CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18398751HCID 18398751, compound

Product 1

HCID 18398756HCID 18398756, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-tert-Butoxycarbonyl-2-bromo-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole (7.12 g) was added to a 1 mol solution of sodium methoxide in methanol (200 ml) and the resulting mixture warmed to 60° C. for 2 h. After cooling the solvent was removed under reduced pressure and the residue purified immediately by flash chromatography (SiO2; n-hexane/ethyl acetate 10:1) to give the product as a pale yellow oil (4.79 g); 1H (250 MHz, CDCl3) δ1.60-2.00 (6H, br m), 3.03 (2H, t, J=7.5 Hz), 3.42 (1H, m), 3.67 (1H, m), 3.78 (1H, m), 3.83 (1H, m), 4.63 (1H, t, J=2.5 Hz), 7.09 (2H, m), 7.25 (1H, d, J=5.0 Hz), 7.58 (1H, d, J=5.0 Hz) and 8.09 (1H, br s).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed under reduced pressure
  3. customthe residue purified immediately by flash chromatography (SiO2; n-hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-91a81bf02f6a4571a6babed021cbe266
Source dataset
uspto-grants-2002_11
Patent number
US06486153B1

Reaction notes

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