Hydrochloric Acid → HCID 69654642, compound

HRID 1244037Notes

Reaction equation

HRID 1244037 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][C:9]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:10]([NH2:16])[CH2:11][CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+].Cl>[OH-].[Pd+2].[OH-].CO>[C:17]1([C@:9]23[NH:8][C@H:13]([CH2:14][CH2:15]2)[CH2:12][CH2:11][C@H:10]3[NH2:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formateHCID 21931720HCID 21931720, compound

Product 1

HCID 69654642HCID 69654642, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 25 ml round bottom flask equipped with nitrogen inlet and condenser was placed 37 mg (0.127 mmol) of either the (1S,2S,5R) (or the (1R,2R,5S)) 8-Benzyl-1-phenyl-8-aza-bicyclo[3.2.1]oct-2-ylamine together with 10 ml of methanol, 80 mg (1.27 mmol) ammonium formate and 12 mg palladium hydroxide. The reaction mixture was treated with 21 ul of conc aq HCl and then heated under reflux for 40 mins and then cooled to room temperature. The suspension was filtered through a bed of celite which was then washed with methanol. The combined organics were evaporated in vacuo and the residue was taken up in chloroform and partitioned with saturated aqueous bicarbonate solution. The organics were washed with saturated brine solution and then dried over a bed of sodium sulfate. The mixture was filtered and the filtrate evaporated in vacuo to afford 20 mg of the desired (1S,2S,5R) (or the (1R,2R,5S)) diamine. 1H NMR (CDCl3, 400 MHz) δ 7.31–7.16 (br.m., 5H), 3.64–3.63 (br.s., 1H), 2.95 (dd, 1H, J=5 Hz, J=2 Hz), 2.25–2.19 (br.m., 1H), 2.03–1.89 (br.m., 2H), 1.87–1.78 (br.m, 5H), 1.72–1.66 (br.m., 1H), 1.54–1.49 (br.m., 1H), 1.33–1.28 (br.m., 1H) ppm. Mass spectrum APCI m/z 203 (p+1).

Workup

  1. customTo a 25 ml round bottom flask equipped with nitrogen inlet and condenser
  2. temperatureheated
  3. temperatureunder reflux for 40 mins
  4. filtrationThe suspension was filtered through a bed of celite which
  5. washwas then washed with methanol
  6. customThe combined organics were evaporated in vacuo
  7. custompartitioned with saturated aqueous bicarbonate solution
  8. washThe organics were washed with saturated brine solution
  9. dry with materialdried over a bed of sodium sulfate
  10. filtrationThe mixture was filtered
  11. customthe filtrate evaporated in vacuo
  12. customto afford 20 mg of the

Sources & evidence

ORD record
ord-6d572a84593d420ab4c8be224cc931df
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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