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

HRID 1985620Notes

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)[C:21]([CH3:24])([CH3:23])[CH3:22])(=O)OC.O.[NH2:27][NH2:28]>>[C:21]([C:20]1[N:27]=[N:28][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)([CH3:24])([CH3:23])[CH3:22]

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 641916Camphoroquinone

HCID 14302170Dimethyl (3,3-dimethyl-2-oxobutyl)phosphonate

Product 1

HCID 69061134(1R,8S)-5-tert-Butyl-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-triene

Procedure

light yellow oil. MS (ESI): 245.2 (MH+). Prepared from (1R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione, (3,3-dimethyl-2-oxo-butyl)-phosphonic acid dimethyl ester, hydrazine monohydrate. Minor product, regioisomer of compound of example 24, isolated and purified by silica gel chromatography.

Sources & evidence

ORD record: ord-7c34052b10674fc3b0b968e3b43da471
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547697B2

Reaction notes

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