Ammonium formate → HCID 118135600, compound

HRID 2279942Notes

Reaction equation

HRID 2279942 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:37])[CH:11]([NH:26]C(OCC1C=CC=CC=1)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18]CC3C=CC=CC=3)[CH:13]=1)[CH2:2]2.C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10](=[O:37])[CH:11]([NH2:26])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)[CH2:2]2

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 118135599HCID 118135599, compound

Product 1

HCID 118135600HCID 118135600, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of [(3R)-quinuclidin-3-yl]2-(benzyloxycarbonylamino)-2-(3-benzyloxyphenyl)acetate (1.5 g, 3.0 mmol) in ethyl acetate (30 mL) were added ammonium formate (945 mg, 15 mmol) and 10% Pd/C (400 mg). The mixture was heated to 60° C. for 16 h. Additional ammonium formate (400 mg, 6.3 mmol) and 10% Pd/C (200 mg) were added and the black slurry stirred at 60° C. for 4 h. After cooling the slurry to room temperature and filtration through a pad of Celite®, the solids were washed with ethyl acetate/ethanol (1:1, 250 mL). The solvent was removed in vacuo to yield the title compound as a yellow oil (800 mg, 97%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling the slurry to room temperature
  2. filtrationfiltration through a pad of Celite®
  3. washthe solids were washed with ethyl acetate/ethanol (1:1, 250 mL)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3fefa9a4814a42cbafcd8589b901f570
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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