Hydrazine hydrate (1:1) → (1S,8R)-5-(3,3-Dimethyl-butyl)-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2,4,6-triene

HRID 1985613Notes

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][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=O)OC.O.[NH2:29][NH2:30]>>[CH3:24][C:23]([CH3:26])([CH3:25])[CH2:22][CH2:21][C:20]1[CH:19]=[C:4]2[C:3]([C@:2]3([CH3:1])[C:8]([CH3:10])([CH3:9])[C@H:5]2[CH2:6][CH2:7]3)=[N:30][N:29]=1

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 1549179(+)-Camphorquinone

HCID 86617461(5,5-Dimethyl-2-oxo-hexyl)-phosphonic acid dimethyl ester

Product 1

HCID 69070145(1S,8R)-5-(3,3-Dimethyl-butyl)-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2,4,6-triene

Procedure

light yellow viscous oil MS (ESI): 273.2 (MH+). Prepared from (1S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione, (5,5-dimethyl-2-oxo-hexyl)-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record: ord-addcbf5ac5b24096920e55dda3ac5478
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547697B2

Reaction notes

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