Acetyl chloride → HCID 68685405, compound

HRID 638961Notes

Reaction equation

HRID 638961 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[C@H:11]([CH2:12][CH3:13])[CH2:10][N:9]1C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([C@H:8]1[C@H:11]([CH2:12][CH3:13])[CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 68685658HCID 68685658, compound

Product 1

HCID 68685405HCID 68685405, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred solution of (+)trans-1-benzhydryl-3-ethylazetidine-2-carboxylic acid tert-butyl ester (2.85 mmol, 1 eq.) in dry MeOH (50 mL) was added 1 M acetyl chloride (3.1 mL, 3.13 mmol, 1.1 eq.) in MeOH and sonicated the mixture to obtain clear solution. To this was added palladium hydroxide on carbon (20% Pd(OH)/C, 200 mg) and the mixture was hydrogenated at 60 psi for 5 h. The catalyst was filtered off and the filtrate was concentrated in vacuo to afford (+)-trans-3-ethylazetidine-2-carboxylic acid tert-butyl ester in quantitative yield. This was used without further purification.

Workup

  1. customsonicated the mixture
  2. customto obtain clear solution
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8179eca4d2d8495ead73ba2fa250cae3
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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