Hydrochloric Acid → HCID 19018591, compound

HRID 1109992Notes

Reaction equation

HRID 1109992 reaction equation
Br.Br[CH2:3][C:4]([C:6]12[CH2:13][N:10]([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=O.Br.O=C(C12CN(CC1)CCC2)C=O.C(=O)(O)O.[NH2:31][NH:32][C:33]([NH2:35])=[NH:34].Cl.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:35][C:33]1[N:32]=[N:31][CH:3]=[C:4]([C:6]23[CH2:13][N:10]([CH2:11][CH2:12]2)[CH2:9][CH2:8][CH2:7]3)[N:34]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 19809490HCID 19809490, compoundHCID 86747939HCID 86747939, compoundHCID 178513185HCID 178513185, compound

Product 1

HCID 19018591HCID 19018591, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(±) 5-(α-Bromoacetyl) -1-azabicyclo[3.2.11octane hydrobromide (1.0 g, 3.2 mmol) was converted into (±) 2-oxo-2-(1-azabicyclo[3.2.1 ]oct-5-yl) ethanal hydrobromide as described in Example 1. The crude aldehyde was immediately treated with a suspension of aminoguanidine bicarbonate (0.46 g, 3.38 mmol) in water (15 ml) and the solution was acidified to pH4 with 5M HCl. After stirring overnight at room temperature the reaction mixture was saturated with potassium carbonate then extracted into chloroform. The combined organic extracts were dried over sodium sulphate, concentrated in vacuo and the residue chromatographed on neutral alumina in a gradient of 0-8% methanol in chloroform. This afforded the title compound (E2) as a solid (95 mg, 15%) which was converted into the oxalate salt m.p. 184° C. (dec) (from methanol-ether)..

Workup

  1. extractionthen extracted into chloroform
  2. dry with materialThe combined organic extracts were dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customthe residue chromatographed on neutral alumina in a gradient of 0-8% methanol in chloroform

Sources & evidence

ORD record
ord-92071a0574c34fa0a5ded470e7e20035
Source dataset
uspto-grants-1994_06
Patent number
US05324724

Reaction notes

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