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

HRID 2243976Notes

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]([CH:22]1[CH2:24][CH2:23]1)=O)(=O)OC.O.[NH2:26][NH2:27]>>[CH:22]1([C:20]2[N:26]=[N:27][C:3]3[C@@:2]4([CH3:1])[C:8]([CH3:10])([CH3:9])[C@@H:5]([C:4]=3[CH:19]=2)[CH2:6][CH2:7]4)[CH2:24][CH2:23]1

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 641916Camphoroquinone

HCID 57624838Dimethyl (2-cyclopropyl-2-oxoethyl)phosphonate

Product 1

HCID 67365663(1R,8S)-5-Cyclopropyl-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-triene

Procedure

colorless oil. MS (EI): 228.3 (M+). Prepared from (1R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione, (2-Cyclopropyl-2-oxo-ethyl)-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record: ord-89907ad70fa744eab992a4da04d07998
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678795B2

Reaction notes

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