Hydrazine hydrate (1:1) → (5RS,8SR)-9,9-dimethyl-3-[(1-methylcyclopropyl)methyl]-5,6,7,8-tetrahydro-5,8-methanocinnoline

HRID 1888887Notes

Reaction equation

HRID 1888887 reaction equation
[CH3:1][C:2]1([CH3:11])[CH:6]2[CH2:7][CH2:8][CH:3]1[C:4](=O)[C:5]2=O.COP([CH2:18][C:19](=O)[CH2:20][C:21]1([CH3:24])[CH2:23][CH2:22]1)(=O)OC.O.[NH2:27][NH2:28]>>[CH3:1][C:2]1([CH3:11])[CH:6]2[CH2:7][CH2:8][CH:3]1[C:4]1[CH:18]=[C:19]([CH2:20][C:21]3([CH3:24])[CH2:23][CH2:22]3)[N:27]=[N:28][C:5]=12

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 38024027,7-Dimethylbicyclo[2.2.1]heptane-2,3-dioneHCID 86638118[3-(1-Methyl-cyclopropyl)-2-oxo-propyl]-phosphonic acid dim ethyl ester

Product 1

HCID 67072219(5RS,8SR)-9,9-dimethyl-3-[(1-methylcyclopropyl)methyl]-5,6,7,8-tetrahydro-5,8-methanocinnoline

Procedure

Light-yellow solid MS (ESI): 243.1 (MH+). Prepared from 7,7-dimethyl-bicyclo[2.2.1]heptane-2,3-dione (R. F. Childs et al., J. Am. Chem. Soc.; 1980; 102; 4159), [3-(1-methyl-cyclopropyl)-2-oxo-propyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record
ord-0ac1fe660e6743689135f06b118c694b
Source dataset
uspto-grants-2013_08
Patent number
US08501940B2

Reaction notes

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