Acetic Acid → N-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-azetidin-2-one

HRID 1493464Notes

Reaction equation

HRID 1493464 reaction equation
[Si:1]([N:8]1[CH:11]([CH2:12][CH2:13][O:14]C(=O)C)[CH2:10][C:9]1=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[O-].[Na+].C(O)(=O)C>CO>[Si:1]([N:8]1[CH:11]([CH2:12][CH2:13][OH:14])[CH2:10][C:9]1=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13051149N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)azetidin-2-one

Product 1

HCID 13104623N-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-azetidin-2-oneYield 54.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)-azetidin-2-one (41.7 g, 0.154 mol) in anhydrous methanol (415 ml) is stirred under a N2 atmosphere with ice-bath cooling. A solution of sodium methoxide (415 mg, 7.7 mmol) in anhydrous methanol (15 ml) is added and the resulting solution is stirred in the cold for 2 more hrs. Acetic acid (2.2 ml) is then added and the solvents are evaporated in vacuo (i.v.). The residue is taken up in EtOAc (300 ml), washed with H2O (4×75 ml), 5% NaHCO3 (75 ml) and brine, dried with MgSO4 and evaporated i.v. to a clear oil (21.3 g). This material is purified by chromatography on a Baker silica gel column (425 g, packed under EtOAc). After a 100 ml forefraction, 25 ml EtOAc fractions are collected every 2.5 mins. Fractions 41-49 yield starting material and fractions 51-90 afford N-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-azetidin- 2-one (19.4 g) as a clear oil: ir (neat) 2.88, 5.73, 5.80, 7.52, 7.67, 7.99, 8.40, 11.95, and 12.18 cm-1 ; nmr (CDCl3) δ0.25 (s,6), 0.98 (s,9), 1.82 (m,2), 2.67 (dd,1), 3.17 (dd,1), 3.67 (t,2), and 3.67 (m,1); mass spectrum m/e 172.

Workup

  1. temperaturecooling
  2. customthe solvents are evaporated in vacuo (i.v.)
  3. washwashed with H2O (4×75 ml), 5% NaHCO3 (75 ml) and brine
  4. dry with materialdried with MgSO4
  5. customevaporated i.v
  6. customThis material is purified by chromatography on a Baker silica gel column (425 g, packed under EtOAc)
  7. customAfter a 100 ml forefraction, 25 ml EtOAc fractions are collected every 2.5 mins
  8. customFractions 41-49 yield

Sources & evidence

ORD record
ord-c834be23f1694568bde307f29bdb638e
Source dataset
uspto-grants-1991_06
Patent number
US05021566

Reaction notes

Loading…