Hydrazine hydrate (1:1) → (1SR,8RS)-5-(1-Cyclopropyl-1-methyl-ethyl)-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2,4,6-triene

HRID 1985617Notes

Reaction equation

HRID 1985617 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=O)[C:2]2=O.COP([CH2:16][C:17](=O)[C:18]([CH:21]1[CH2:23][CH2:22]1)([CH3:20])[CH3:19])(=O)OC.O.[NH2:26][NH2:27]>C(O)(C)C.CCCCCCC>[CH:21]1([C:18]([C:17]2[CH:16]=[C:3]3[C:2]([CH:1]4[CH2:7][CH:4]3[CH2:5][CH2:6]4)=[N:27][N:26]=2)([CH3:20])[CH3:19])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 138696Bicyclo(2.2.1)heptane-2,3-dioneHCID 86617462(3-Cyclopropyl-3-methyl-2-oxo-butyl)-phosphonic acid dimethyl ester

Product 1

HCID 69063186(1SR,8RS)-5-(1-Cyclopropyl-1-methyl-ethyl)-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2,4,6-triene

Reagents, catalysts & solvents 1

HCID 21225753Isopropanol heptaneSolvent

Procedure

white solid. MS (ESI): 229.2 (MH+). Prepared from bicyclo[2.2.1]heptan-2,3-dione, (3-cyclopropyl-3-methyl-2-oxo-butyl)-phosphonic acid dimethyl ester, hydrazine monohydrate. Submission of the racemate to preparative HPLC, using a chiral column, Chiralpak AD, with 5% isopropanol/heptane as eluant gave the two enantiomers, in optically pure form.

Sources & evidence

ORD record
ord-c132609ff7a24d5abb44bf35bb1b035a
Source dataset
uspto-grants-2009_06
Patent number
US07547697B2

Reaction notes

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