2-Hydrazino-delta-2-imidazoline hydrobromide → (1S,3aS,5S,7aR)-1-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]-7a-methyl-5-phenyl-2,3,4,5,6,7-hexahydro-1H-inden-3a-ol;hydrobromide

HRID 725174Notes

Reaction equation

HRID 725174 reaction equation
[BrH:1].[NH:2]([C:4]1[NH:5][CH2:6][CH2:7][N:8]=1)[NH2:3].[CH:9]([C@@H:11]1[C@:19]2([CH3:20])[C@@:14]([OH:27])([CH2:15][C@@H:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:18]2)[CH2:13][CH2:12]1)=O>O.O1CCOCC1>[BrH:1].[NH:8]1[CH2:7][CH2:6][N:5]=[C:4]1[NH:2]/[N:3]=[CH:9]/[C@@H:11]1[C@:19]2([CH3:20])[C@@:14]([OH:27])([CH2:15][C@@H:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:17][CH2:18]2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 30850992-Hydrazino-delta-2-imidazoline hydrobromideHCID 11054353(1S,3aS,5S,7aR)-1-formyl-5-phenyl-7a-methylperhydroinden-3a-ol

Product 1

HCID 88125924(1S,3aS,5S,7aR)-1-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]-7a-methyl-5-phenyl-2,3,4,5,6,7-hexahydro-1H-inden-3a-ol;hydrobromideYield 53.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 0.93 g of 2-hydrazino-2-imidazoline hydrobromide in 45 ml of water and 30 ml of dioxane a solution of 0.89 g of (1S,3aS,5S,7aR)-1-formyl-5-phenyl-7a-methylperhydroinden-3a-ol in 30 ml of dioxane was added dropwise at room temperature and the mixture was stirred for 2 hrs. The solution was evaporated to dryness under reduced pressure and the residue was ground with ethanol/water then with ethanol to give 0.78 g of the title compound (I-al) as a white solid.

Workup

  1. customThe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7f73c64bcc17405682189bb5c0f0dd00
Source dataset
uspto-grants-1998_01
Patent number
US05705531

Reaction notes

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