benzyl tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrole-6(3H)-carboxylate → hexahydro-2H-[1,4]dioxino[2,3-c]pyrrole

HRID 712398Notes

Reaction equation

HRID 712398 reaction equation
[O:1]1[CH:6]2[CH2:7][N:8](C(OCC3C=CC=CC=3)=O)[CH2:9][CH:5]2[O:4][CH2:3][CH2:2]1>CO.C(O)=O.[OH-].[OH-].[Pd+2]>[O:1]1[CH:6]2[CH2:7][NH:8][CH2:9][CH:5]2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 86729466benzyl tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrole-6(3H)-carboxylate

Product 1

HCID 82418726hexahydro-2H-[1,4]dioxino[2,3-c]pyrrole

Reagents, catalysts & solvents 3

HCID 284Formic AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrole-6(3H)-carboxylate (0.46 g, 1.94 mmol) in MeOH (20 mL) was added two drops of HCO2H followed by 20% Pd(OH)2 (50 mg). The reaction mixture was stirred under H2 for 4 h at rt and was filtered. The filtrate was concentrated in vacuo to give the crude product, which was used for the next step without further purification.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-75bb0a9810e448979dfa71fb2945391d
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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