Ammonium formate → HCID 85850735, compound

HRID 1454342Notes

Reaction equation

HRID 1454342 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH:8]1[CH2:12][CH2:11][CH:10]([P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 85850734HCID 85850734, compound

Product 1

HCID 85850735HCID 85850735, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3 g (10 mmol) of (R/S)-1-benzyl-pyrrolidin-3-ylphosphonic acid, diethyl ester (from Step A), 9.5 g (150 mmol) of ammonium formate and 1.0 g of 10% palladium on charcoal in 60 mL of MeOH was warmed to 40° C. for 1.5 h. The reaction was cooled, filtered through a pad of celite and concentrated. The mixture was partitioned between 75 mL of 1N NaOH and 100 mL of CH2Cl2. After separating layers, the aqueous phase was extracted with 3×100 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified on a 40M Biotage column using 90:10:1 v/v/v CH2Cl2/MeOH/NH4OH as the eluant to afford the title compound as a pale yellow oil: RF: 0.13 (95:5:0.5 v/v/v CH2Cl2MeOH/NH4OH); 1H-NMR (500 MHz) δ 1.22 (t, J=7.1, 6H), 1.81 (m, 1H), 1.95 (m, 1H), 2.25 (m, 1H), 2.73 (m, 1H), 2.89-2.99 (m, 3H), 4.06-4.16 (m, 4H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated
  4. customThe mixture was partitioned between 75 mL of 1N NaOH and 100 mL of CH2Cl2
  5. customAfter separating layers
  6. extractionthe aqueous phase was extracted with 3×100 mL of CH2Cl2
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified on a 40M Biotage column

Sources & evidence

ORD record
ord-d7d7edcc14e5464398db2bb3516e0af3
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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