Nitrogen → tert-Butyl pyrazolidine-3-carboxylate

HRID 1396841Notes

Reaction equation

HRID 1396841 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:5][CH2:4][CH:3]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[N:2]1C(OCC1C=CC=CC=1)=O.N#N>CO.[Pd]>[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[NH:2]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 683499043-(1,1-Dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylate

Product 1

HCID 57015512tert-Butyl pyrazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(1,1-dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylate (2.00 kg, 4.54 mol) in 10 L methanol was charged into a 20 L four-necked round-bottomed flask under N2 (gas). Then 200 g Pd/C (10%, 65% water) was added carefully to the mixture solution. H2 (gas) was introduced to exchange N2 (gas) three times. The mixture solution was allowed to react at 25° C. under 1 atm of H2 for 8 h until the starting material was consumed completely. N2 (gas) was introduced to remove excess H2 (gas). A filtration was performed to remove the catalyst. The filtrate can be used in the next step without further purification.

Workup

  1. additionH2 (gas) was introduced
  2. customto react at 25° C. under 1 atm of H2 for 8 h until the starting material
  3. customwas consumed completely
  4. additionN2 (gas) was introduced
  5. customto remove excess H2 (gas)
  6. filtrationA filtration
  7. customto remove the catalyst
  8. customThe filtrate can be used in the next step without further purification

Sources & evidence

ORD record
ord-f9bab92cb33c45da986d67329f3c4e90
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

Loading…