Trifluoroacetic acid → 3-((tert-Butyldimethylsilanyl)oxy)azetidine

HRID 1261358Notes

Reaction equation

HRID 1261358 reaction equation
[Si:1]([O:8][CH:9]1[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Si:1]([O:8][CH:9]1[CH2:12][NH:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59424599tert-Butyl 3-(tert-butyldimethylsilyloxy)azetidine-1-carboxylate

Product 1

HCID 574386563-((tert-Butyldimethylsilanyl)oxy)azetidineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 295 (200 mg, 0.696 mol), DCM (1 mL) and TFA (1 mL) was stirred for 1 h at room temperature, concentrated under reduced pressure; NaOH (1M, 15 mL) was added to the residue and the suspension was extracted with DCM, the extract was dried (anhydrous Na2SO4) and concentrated, to afford title compound 296 (90.4 mg, 69% yield) as a syrup. MS (m/z): 188.1 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionNaOH (1M, 15 mL) was added to the residue
  3. extractionthe suspension was extracted with DCM
  4. dry with materialthe extract was dried (anhydrous Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b6f3fc0983545a4959a3b4c227804be
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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