p-Toluenesulfonic acid → HCID 15951437, compound

HRID 2243904Notes

Reaction equation

HRID 2243904 reaction equation
[C:1]12([C:11](=O)/[CH:12]=[C:13]3/[C:14](=O)[C@:15]4([CH3:22])[C:19]([CH3:21])([CH3:20])[C@H:18]/3[CH2:17][CH2:16]4)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[NH2:26][NH2:27].C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]12([C:11]3[CH:12]=[C:13]4[C:14]([C@:15]5([CH3:22])[C:19]([CH3:21])([CH3:20])[C@H:18]4[CH2:17][CH2:16]5)=[N:27][N:26]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 24654Hydrazine hydrate (1:1)HCID 10942334Sodium MethoxideHCID 67364818HCID 67364818, compound

Product 1

HCID 15951437HCID 15951437, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This material was prepared according to example 1 step C] (1S,4R)-3-[2-adamantan-1-yl-2-oxo-eth-(E)-ylidene]-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one (0.2 g) and hydrazine monohydrate (0.117 g) with the following modifications: toluene as solvent (5 ml) in the presence of p-toluene sulfonic acid (0.117 g), heating for 12 h at reflux temperature and isolation of desired product by chromatography (no further NaOMe treatment as in example 1 step C]. This gave (1S,8R)-5-adamantan-1-yl-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2,4,6-triene (0.027 g) as an amorphous light yellow solid. MS (EI): 322.4 (M+).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-75a71169a25741c99b10ccb34f66b410
Source dataset
uspto-grants-2010_03
Patent number
US07678795B2

Reaction notes

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