Acetic Acid → HCID 59559320, compound

HRID 2075180Notes

Reaction equation

HRID 2075180 reaction equation
C([N:14]1[CH2:17][C:16]([OH:22])([C:18]([O:20][CH3:21])=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[OH:22][C:16]1([C:18]([O:20][CH3:21])=[O:19])[CH2:17][NH:14][CH2:15]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59559322HCID 59559322, compound

Product 1

HCID 59559320HCID 59559320, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A reactor was charged with methyl 1-benzhydryl-3-hydroxyazetidine-3-carboxylate (1.6 g, 5.4 mmol), 10% Pd/C (0.300 g, 2.8 mmol), and glacial acetic acid (0.300 mL, 5.2 mmol) in MeOH (30 mL). The mixture was allowed to stir for 3 h under 50 psig of H2. The crude was filtered through Celite and rinsed with MeOH. After evaporation, the solid was rinsed with Et2O to give methyl 3-hydroxyazetidine-3-carboxylate as the acetic acid salt. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.74 (d, J=9.1 Hz, 2H), 3.69 (s, 3H), 3.44 (d, J=8.9 Hz, 2H), 1.88 (s, 3H).

Workup

  1. filtrationThe crude was filtered through Celite
  2. washrinsed with MeOH
  3. customAfter evaporation
  4. washthe solid was rinsed with Et2O

Sources & evidence

ORD record
ord-8e51eead256544e7b7e2dda68d46fd2c
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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