Hydrazine hydrate (1:1) → (1S,8R)-5-Cyclopropylmethyl-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-triene

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][CH:22]1[CH2:24][CH2:23]1)(=O)OC.O.[NH2:27][NH2:28]>>[CH:22]1([CH2:21][C:20]2[N:27]=[N:28][C:3]3[C@:2]4([CH3:1])[C:8]([CH3:10])([CH3:9])[C@H:5]([C:4]=3[CH:19]=2)[CH2:6][CH2:7]4)[CH2:24][CH2:23]1

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 1549179(+)-Camphorquinone

HCID 86617460(3-Cyclopropyl-2-oxo-propyl)-phosphonic acid dimethyl ester

Product 1

HCID 69063534(1S,8R)-5-Cyclopropylmethyl-1,11,11-trimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-triene

Procedure

Yellow solid. MS (ESI): 243.2 (MH+). Prepared from (1S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione, [(3-cyclopropyl-2-oxo-propyl)-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record: ord-1c1f4f70cbc646d8a54a41eedf6f116c
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547697B2

Reaction notes

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