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

HRID 1888889Notes

Reaction equation

HRID 1888889 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[C:3](=O)[C:2]2=O.COP([CH2:16][C:17](=O)[CH2:18][C:19]1([CH3:22])[CH2:21][CH2:20]1)(=O)OC.O.[NH2:25][NH2:26]>>[CH3:22][C:19]1([CH2:18][C:17]2[N:25]=[N:26][C:2]3[CH:1]4[CH2:7][CH:4]([C:3]=3[CH:16]=2)[CH2:5][CH2:6]4)[CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 68535573(1S,4R)-bicyclo[2.2.1]heptan-2,3-dioneHCID 86638118[3-(1-Methyl-cyclopropyl)-2-oxo-propyl]-phosphonic acid dim ethyl ester

Product 1

HCID 46175498(5RS,8SR)-3-[(1-methylcyclopropyl)methyl]-5,6,7,8-tetrahydro-5,8-methanocinnoline

Procedure

Light-yellow solid MS (ESI): 215.2 (MH+). Prepared from (1S,4R)-bicyclo[2.2.1]heptan-2,3-dione (M. Hanack et al, Justus Liebigs Annalen der Chemie; 1973; 1557), [3-(1-methyl-cyclopropyl)-2-oxo-propyl]-phosphonic acid dim ethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record
ord-9d64f232d0794a438a010687da38df02
Source dataset
uspto-grants-2013_08
Patent number
US08501940B2

Reaction notes

Loading…