Hydrazine hydrate (1:1) → (1S,8R)-1,11,11-Trimethyl-5-(1-methyl-1H-pyrrol-2-yl)-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2,4,6-triene

HRID 2243934Notes

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]([C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)=O)(=O)OC.O.[NH2:29][NH2:30]>>[CH3:1][C@@:2]12[C:8]([CH3:10])([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[C:4]1[C:3]2=[N:29][N:30]=[C:20]([C:22]2[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=2)[CH:19]=1

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 1549179(+)-Camphorquinone

HCID 86609923[2-(1-Methyl-1H-pyrrol-2-yl)-2-oxo-ethyl]-phosphonic acid dimethyl ester

Product 1

HCID 67363736(1S,8R)-1,11,11-Trimethyl-5-(1-methyl-1H-pyrrol-2-yl)-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2,4,6-triene

Procedure

light brown amorphous solid. MS (EI): 267.2 (M+). Prepared from (1S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione, [2-(1-Methyl-1H-pyrrol-2-yl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record: ord-bc7ef81a213b49ebbf8687aa05976eac
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678795B2

Reaction notes

Loading…