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

HRID 500914Notes

Reaction equation

HRID 500914 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 wit 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 wit EtOAc/hexane (9:1) to EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-b4d3cbb5c2204937b42c5cab58e190eb
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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