tert-Butyldimethylsilyl chloride → tert-Butyl 3-(tert-butyldimethylsilyloxy)azetidine-1-carboxylate

HRID 1711062Notes

Reaction equation

HRID 1711062 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:17]([O:1][CH:2]1[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]1)([C:14]([CH3:16])([CH3:15])[CH3:13])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 59424599tert-Butyl 3-(tert-butyldimethylsilyloxy)azetidine-1-carboxylateYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (1 g, 5.77 mmol), TBSCl (6.35 mmol, 956 mg) in DCM (11.5 mL), was stirred for 72 hrs at room temperature. The solvent was removed under reduced pressure, EtOAc was added to the residue, and the solid material was removed by filtration. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography with gradient elution with EtOAc/hexane (9:1) to EtOAc/hexane (1:1), to afford title compound 295 (1.25 g, 75% yield) as a syrup. MS (m/z): 310.1 (M+23).

Workup

  1. customThe solvent was removed under reduced pressure, EtOAc
  2. additionwas added to the residue
  3. customthe solid material was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography with gradient elution with EtOAc/hexane (9:1) to EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-fb106b802a154c36b4c40c17ecacca97
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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