Aluminium lithium hydride → 6-Benzyloxytryptamine

HRID 1371915Notes

Reaction equation

HRID 1371915 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N+:7]([CH:10]=[CH:11][C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:19]=2)[NH:14][CH:13]=1)([O-])=O>C1COCC1>[CH2:22]([O:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[C:12]([CH2:11][CH2:10][NH2:7])=[CH:13][NH:14]2)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67443454HCID 67443454, compound

Product 1

HCID 33605186-BenzyloxytryptamineYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Add to a mixture of LAH (6.2 g, 163.1 mmol) and 300 mL dry THF a solution of 3-(2-nitrovinyl)-6-benzyloxy-1H-indole (9 g, 30.6 mmol) in 200 mL THF. Reflux the mixture overnight and then cool to 0° C. and quench sequentially with 6.2 mL water, 6.2 mL 15% aqueous NaOH and 18.6 mL water. After stirring 2 hours, filter through celite and concentrate to give 7.9 g (96%) of the title compound as an oil: 1H NMR (CDCl3) 8.06 (bs, 1H), 7.47–7.43 (m, 3H), 7.38–7.35 (m, 2H), 7.32–7.28 (m, 1H), 6.88–6.84 (m, 3H), 5.08 (s, 2H), 3.01–2.97 (m, 2H), 2.87–2.83 (m, 2H), 1.6 (bs, 2H).

Workup

  1. temperatureReflux the mixture overnight
  2. customquench sequentially with 6.2 mL water, 6.2 mL 15% aqueous NaOH and 18.6 mL water
  3. filtrationfilter through celite
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-91aade630373404aaaec8391fe055300
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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