Hydrochloric Acid → tert-Butyl pyrazolidine-3-carboxylate

HRID 1396845Notes

Reaction equation

HRID 1396845 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.[H][H].Cl.CCOCC>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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 683499043-(1,1-Dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57015512tert-Butyl pyrazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(1,1-Dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylate (5.30 g, 12.03 mmol) was dissolved in methanol (100 mL) and 10% Pd/C (degussa type) (1.06 g, 0.996 mmol) was added. The mixture was stirred under a balloon of hydrogen for 60 min. LCMS showed clean deprotection. HCl in ether (6.02 mL, 12.03 mmol) was added, and the mixture was stirred 5 min. The catalyst was filtered off and the filtrate was evaporated, yielding 1,1-dimethylethyl 3-pyrazolidinecarboxylate.HCl (2.45 g, 11.74 mmol, 98% yield) as an orange solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9dcfd5673d374a8d80601b358df6b6a9
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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