Sodium borohydride → Isoellipticine

HRID 1089904Notes

Reaction equation

HRID 1089904 reaction equation
O[C:2]1([CH3:21])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5](O)([CH3:15])[C:4]2[CH:17]=[N:18][CH:19]=[CH:20][C:3]1=2.[BH4-].[Na+]>C(O)C>[CH3:21][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([CH3:15])=[C:4]2[CH:17]=[N:18][CH:19]=[CH:20][C:3]=12

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19978651HCID 19978651, compound

Product 1

HCID 265286Isoellipticine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A similar reaction to that described above starting from the compounds of formulae XXVII and XXVIII appears in J. Org. Chem. 48, pp. 2690-2695 (1983) in which an equivalent of 5,11-dihydroxy 5,11-dimethyl 10,11-dihydro 5H-pyrido[3,4-b]carbazole is made to react with about 40 equivalents of sodium borohydride for 20 hours in refluxing ethanol to give rise to 5,11 dimethyl 10H-pyrido[3,4-b]carbazole.

Workup

  1. customA similar reaction to

Sources & evidence

ORD record
ord-008908feef394962a37fbffbfe984404
Source dataset
uspto-grants-1992_01
Patent number
US05079363

Reaction notes

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