Ammonium formate → 4-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester

HRID 457430Notes

Reaction equation

HRID 457430 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[C:13]([N+:25]([O-])=O)[C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][C:16]=32)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[C:13]([NH2:25])[C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][C:16]=32)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69030373HCID 69030373, compound

Product 1

HCID 542004584-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl esterYield 100.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

4-Butylamino-5-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (460 mg, 1.27 mmol) was treated with ammonium formate (850 mg, 12.7 mmol) and 10% Pd(OH)2/C (50 mg) in methanol (20 mL) and brought to reflux for 1 hour then filtered through a Celite pad and concentrated. The solids were treated with saturated aqueous Na2CO3 solution, extracted with CH2Cl2 (3×30 mL) and dried by filtration through a cotton plug to give an oil (440 mg, 100%).

Workup

  1. temperatureto reflux for 1 hour
  2. filtrationthen filtered through a Celite pad
  3. concentrationconcentrated
  4. additionThe solids were treated with saturated aqueous Na2CO3 solution
  5. extractionextracted with CH2Cl2 (3×30 mL)
  6. customdried by filtration through a cotton plug

Sources & evidence

ORD record
ord-e0ad4d84b33249aaab47a732a454d722
Source dataset
uspto-grants-2007_03
Patent number
US07186870B2

Reaction notes

Loading…