Sodium borohydride → Carmoxirole

HRID 1657007Notes

Reaction equation

HRID 1657007 reaction equation
[BH4-].[Na+].[Br-].[C:4]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][CH2:18][CH2:19][N+:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)([OH:6])=[O:5]>O.[OH-].[Na+]>[C:26]1([C:23]2[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][C:10]3[C:9]4[C:13](=[CH:14][CH:15]=[C:7]([C:4]([OH:6])=[O:5])[CH:8]=4)[NH:12][CH:11]=3)[CH2:21][CH:22]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19786638HCID 19786638, compound

Product 1

HCID 57364Carmoxirole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

1 g of NaBH4 in 20 ml of water is added, with stirring, to a solution of 4.51 g of 1-[4-(5-carboxy-3-indolyl)-butyl]-4-phenylpyridinium bromide [obtainable from 3-(4-bromobutyl)-indole-5-carboxylic acid and 4-phenylpyridine] in 50 ml of 1N NaOH, and stirring is continued for a further 3 hours at 60°. Working up in the customary manner gives 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridyl)-butyl]-indole-5-carboxylic acid, m.p. 284°-285°.

Sources & evidence

ORD record
ord-5b0f9637b65c4250b858b3fc5c2168f1
Source dataset
uspto-grants-1993_10
Patent number
US05256673

Reaction notes

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