Sodium Hydroxide → 2-[4-(5-Hydroxymethyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine

HRID 649637Notes

Reaction equation

HRID 649637 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][C:20]2[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[O:25][C:19]=2[CH2:18]1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[OH:2][CH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][C:20]2[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[O:25][C:19]=2[CH2:18]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21243293HCID 21243293, compound

Product 1

HCID 212432642-[4-(5-Hydroxymethyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.88 g of 2-[4-(5-carboxy-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine in 40 ml of THF is added dropwise to a stirred suspension of 0.76 g of lithium aluminium hydride in 30 ml of THF under N2. The mixture is then stirred at 20° for 2 hours, decomposition is carried out with dilute sodium hydroxide solution and then with water, and the mixture is filtered. The usual working up is carried out on the filtrate. 2-[4-(5-Hydroxymethyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine is obtained.

Workup

  1. filtrationwith water, and the mixture is filtered

Sources & evidence

ORD record
ord-ff194621e7c94b138d21c3e375b1d911
Source dataset
uspto-grants-1988_04
Patent number
US04740602

Reaction notes

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