HCID 22220462, compound → 3-((tert-Butyldimethylsilanyl)oxy)azetidine

HRID 1013112Notes

Reaction equation

HRID 1013112 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[Si:19]([O:18][CH:16]1[CH2:17][NH:14][CH2:15]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 22220462HCID 22220462, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 574386563-((tert-Butyldimethylsilanyl)oxy)azetidineYield 43.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×

Procedure

Add 20% palladium hydroxide on activated carbon (0.946 g) and ethanol (20 mL) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the mixture at RT for 15 min. Vent the hydrogen from the reaction vessel and purge the reaction vessel with nitrogen. Add 1-benzhydryl-3-(tert-butyl-dimethylsilanyloxy)-azetidine (3.89 g, 0.0110 mol) and ethanol (80 mL) to the pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the reaction at RT for 6 h. Turn off the agitation, vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Sample the reaction mixture for analysis. Once the reaction is shown to be complete, filter the reaction mixture to remove the catalyst, concentrate and purify (silica gel chromatography, eluting with 5:95 to 10:90 2 M ammonia in methanol:DCM) to give the title compound (889 mg, 43%).

Workup

  1. customPurge the reaction vessel with nitrogen
  2. customseal the vessel
  3. custompurge the reaction vessel with nitrogen
  4. customPurge the reaction vessel with nitrogen
  5. customseal the vessel
  6. stirringagitate
  7. customthe reaction at RT for 6 h
  8. custompurge the vessel with nitrogen
  9. filtrationfilter the reaction mixture
  10. customto remove the catalyst
  11. concentrationconcentrate
  12. custompurify
  13. wash(silica gel chromatography, eluting with 5:95 to 10:90 2 M ammonia in methanol:DCM)

Sources & evidence

ORD record
ord-266e70e53af34c0e881a7a78d88d74ba
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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