Hydrazine hydrate (1:1) → (1R,8S)-5-(2,2-Dimethyl-propyl)-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-triene

HRID 1985618Notes

Reaction equation

[CH3:1][C@:2]12[C:8]([CH3:10])([CH3:9])[C@H:5]([CH2:6][CH2:7]1)[C:4](=O)[C:3]2=O.COP([CH2:19][C:20](=O)[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=O)OC.O.[NH2:28][NH2:29]>>[CH3:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]1[N:28]=[N:29][C:3]2[C@@:2]3([CH3:1])[C:8]([CH3:10])([CH3:9])[C@@H:5]([C:4]=2[CH:19]=1)[CH2:6][CH2:7]3

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 641916Camphoroquinone

HCID 25112585(4,4-Dimethyl-2-oxo-pentyl)-phosphonic acid dimethyl ester

Product 1

HCID 69059732(1R,8S)-5-(2,2-Dimethyl-propyl)-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-triene

Procedure

white solid. MS (ESI): 259.1 (MH+). Prepared from (1R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione, (4,4-dimethyl-2-oxo-pentyl)-phosphonic acid dimethyl ester, hydrazine monohydrate. Minor product, regioisomer of compound of example 22, isolated and purified by silica gel chromatography.

Sources & evidence

ORD record: ord-0a66d3d56a3346c184ff2578d079245a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547697B2

Reaction notes

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