1-Benzyloxycarbonyl-3-t-butyldiphenylsilyloxyazetidine → 3-((Tert-butyldiphenylsilyl)oxy)azetidine

HRID 891690Notes

Reaction equation

HRID 891690 reaction equation
C(OC([N:11]1[CH2:14][CH:13]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[Si:16]([O:15][CH:13]1[CH2:12][NH:11][CH2:14]1)([C:29]([CH3:32])([CH3:30])[CH3:31])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 222429801-Benzyloxycarbonyl-3-t-butyldiphenylsilyloxyazetidine

Product 1

HCID 178425313-((Tert-butyldiphenylsilyl)oxy)azetidineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyloxycarbonyl-3-t-butyldiphenylsilyloxyazetidine (4.04 g, 9.07 mmol) in methanol (200 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (4.04 g) at room temperature for 1.5 hours. After checking the completion of the reaction, the reaction mixture was filtered and the filtrate concentrated under reduced pressure, and the obtained residue was dried under reduced pressure to give 3-t-butyldiphenylsilyloxyazetidine (2.70 g, yield 96%) as a colorless oil.

Workup

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customthe obtained residue was dried under reduced pressure

Sources & evidence

ORD record
ord-ceb202c0d7184921b257f679182172b6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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