Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]-3-hydroxyazetidine-1-carboxylate → 3-[2-(1,3-Dioxolan-2-yl)-1-hydroxyethyl]azetidin-3-ol

HRID 1809024Notes

Reaction equation

HRID 1809024 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]([C:9]1([OH:23])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)[OH:8]>CO.[Pd]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]([C:9]1([OH:23])[CH2:12][NH:11][CH2:10]1)[OH:8]

Participants

4

Reactant 1

HCID 67051562Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]-3-hydroxyazetidine-1-carboxylate

Product 1

HCID 670517803-[2-(1,3-Dioxolan-2-yl)-1-hydroxyethyl]azetidin-3-olYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]-3-hydroxyazetidine-1-carboxylate (235 mg, 0.728 mmol) was dissolved in methanol (5 mL) and treated with 5 wt % palladium on carbon (50 mg) under hydrogen at ambient for 1.5 h. The mixture was filtered and the filtrate was concentrated in vacuo to afford 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]azetidin-3-ol (0.729 mmol): MS (EI) for C8H15NO4: 190 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a06729a924774009879897c181ab1a54
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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