Ammonium formate → HCID 40425273, compound

HRID 339018Notes

Reaction equation

HRID 339018 reaction equation
C([N:8]1[CH2:12][CH2:11][C@:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH2:13][OH:14])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[OH:14][CH2:13][C@@:10]1([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 52276234HCID 52276234, compound

Product 1

HCID 40425273HCID 40425273, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-tert-butyl 1-benzyl-3-(hydroxymethyl)pyrrolidin-3-ylcarbamate (387 mg, 1.26 mmol), 10% Pd/C (134 mg, 0.126 mmol), ammonium formate (398 mg, 6.32 mmol) and MeOH (10 mL) was heated at reflux under nitrogen for 3 hours. After cooling, the reaction mixture was filtered through Celite®. The filtrate was concentrated under reduced pressure. The residue was taken up in DCM and filtered through Celite again. Removal of the solvent gave (R)-tert-butyl 3-(hydroxymethyl)pyrrolidin-3-ylcarbamate (260 mg, 95%), which was used in the next Step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through Celite®
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. filtrationfiltered through Celite again
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-6de5baf49a4e461b89aedd3d90c3117e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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