Ammonium formate → HCID 69950958, compound

HRID 479944Notes

Reaction equation

HRID 479944 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([CH:15]1[CH2:18][N:17](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16]1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.ClCCl.[Pd]>[C:1]([O:5][C:6](=[O:32])[N:7]([CH:15]1[CH2:18][NH:17][CH2:16]1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 69952843HCID 69952843, compound

Product 1

HCID 69950958HCID 69950958, compoundYield 91.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-Benzhydryl-azetidin-3-yl)-benzyl-carbamic acid tert-butyl ester (0.43 g, 1 mmol) in a mixture of methanol (18 ml) and dichloromethane (2 ml) was added ammonium formate (1.3 g, 20 mmol), and 0.15 g of 10% Pd/C. The mixture was stirred at reflux for 18 h. After cooling to room temperature, it was filtered through Celite. The solvents were evaporated, and the residue was washed with hexanes and then extracted with dichloromethane. The dichloromethane solution was evaporated to give 0.24 g of a white solid; m.p. 144-145° C.; MS (ES) m/z 263.0 (MH+).

Workup

  1. temperatureat reflux for 18 h
  2. filtrationit was filtered through Celite
  3. customThe solvents were evaporated
  4. washthe residue was washed with hexanes
  5. extractionextracted with dichloromethane
  6. customThe dichloromethane solution was evaporated

Sources & evidence

ORD record
ord-a63a34b75a6c4fd1b2792799f1bde7a9
Source dataset
uspto-grants-2003_11
Patent number
US06649603B2

Reaction notes

Loading…