Diethyl Ether → 2-Cyclopropyl-3-phenyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene

HRID 600068Notes

Reaction equation

HRID 600068 reaction equation
C(O[C:6]([NH:8][NH:9][CH:10]1[CH2:12][CH2:11]1)=O)(C)(C)C.C(OC(N1C([C:23]2[CH:28]=[CH:27][C:26]([C:29]#N)=[CH:25][CH:24]=2)O1)=O)(C)(C)C.[CH:31]1([NH2:34])[CH2:33][CH2:32]1.[CH3:35][CH2:36]OCC>>[CH:10]1([N:9]2[C:29]([C:26]3[CH:25]=[CH:24][CH:23]=[CH:28][CH:27]=3)=[C:33]3[C:6]([CH2:35][CH2:36][NH:34][CH2:31][CH2:32]3)=[N:8]2)[CH2:11][CH2:12]1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 69828CyclopropylamineHCID 2725038N-Boc-3-(4-cyanophenyl)oxaziridineHCID 67269188tert-Butyl 2-cyclopropylhydrazinecarboxylate

Product 1

HCID 597526382-Cyclopropyl-3-phenyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene

Procedure

N′-cyclopropyl-hydrazinecarboxylic acid tert-butyl ester. To a solution of 1.37 g of 3-(4-cyano-phenyl)-oxaziridine-2-carboxylic acid tert-butyl ester in Et2O (8 mL) was added 1.2 mL of cyclopropylamine. The mixture was aged for 2 h and then concentrated in vacuo. Chromatography on SiO2 (0 to 25% EtOAc/hexanes) provided an impure pale yellow solid that was sublimed under high vacuum in a 50° C. oil bath to afford 641 mg of the desired compound. 1H NMR (500 MHz, CDCl3): 6.31 (br s, 1H), 3.49 (br s, 1H), 2.74 (br s, 1H), 1.48 (s, 9H), 0.52-0.48 (m, 4H).

Workup

  1. concentrationconcentrated in vacuo
  2. customChromatography on SiO2 (0 to 25% EtOAc/hexanes) provided an impure pale yellow solid
  3. customthat was sublimed under high vacuum in a 50° C.

Sources & evidence

ORD record
ord-f5bada61980f4665b18580b4e5cc25b7
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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