Sodium borohydride → racemic trans 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one

HRID 1808768Notes

Reaction equation

HRID 1808768 reaction equation
[NH:1]1[C:10]2=[CH:11][CH:12]=[CH:13][C:8]3=[C:9]2[N:3]([CH2:4][CH2:5][C:6](=[N:15]O)[C:7]3=[O:14])[C:2]1=[O:17].[H][H].[BH4-].[Na+]>[Pd]>[NH2:15][C@H:6]1[C@H:7]([OH:14])[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]3[NH:1][C:2](=[O:17])[N:3]([C:9]=23)[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 72256353CID 72256353HCID 178418361HCID 178418361, compound

Product 1

HCID 59325228racemic trans 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using the methods reported in U.S. Pat. No. 4,585,770, 5,6-dihydro-imidazo[4,5,1-jk][1]benzazepin-2,7-[1H,4H]-dione may be reacted with an alkyl nitrite (e.g., tert-butyl nitrite or isoamyl nitrite), in the presence of a base or acid (e.g., HCl), to form 4,5-dihydro-imidazo[4,5,1-jk][1]benzazepin-2,6,7[1H]-trione-6-oxime. The 4,5-dihydro-imidazo[4,5,1-jk][1]benzazepin-2,6,7[1H]-trione-6-oxime, in turn, is reduced via catalytic hydrogenation (with, for example, hydrogen in the presence of palladium on carbon) or sodium borohydride to form racemic trans 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one:

Sources & evidence

ORD record
ord-f36b6fca23f04487896d585aadcef0a6
Source dataset
uspto-grants-2013_01
Patent number
US08362006B2

Reaction notes

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