Hydrazine hydrate (1:1) → (5r,8s)-8,9,9-Trimethyl-3-[(1-methylcyclopropyl)methyl]-5,6,7,8-tetrahydro-5,8-methanocinnoline

HRID 1888888Notes

Reaction equation

HRID 1888888 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][C:22]1([CH3:25])[CH2:24][CH2:23]1)(=O)OC.O.[NH2:28][NH2:29]>>[CH3:1][C@:2]12[C:8]([CH3:10])([CH3:9])[C@H:5]([C:4]3[CH:19]=[C:20]([CH2:21][C:22]4([CH3:25])[CH2:24][CH2:23]4)[N:28]=[N:29][C:3]=31)[CH2:6][CH2:7]2

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 1549179(+)-CamphorquinoneHCID 86638118[3-(1-Methyl-cyclopropyl)-2-oxo-propyl]-phosphonic acid dim ethyl ester

Product 1

HCID 67071999(5r,8s)-8,9,9-Trimethyl-3-[(1-methylcyclopropyl)methyl]-5,6,7,8-tetrahydro-5,8-methanocinnoline

Procedure

Light-yellow solid MS (ESI): 257.1 (MH+). Prepared from (1S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione (commercially available), [3-(1-methyl-cyclopropyl)-2-oxo-propyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record
ord-36c4a9760a834170915e5152c136bcdd
Source dataset
uspto-grants-2013_08
Patent number
US08501940B2

Reaction notes

Loading…