Sodium Methoxide → N-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-azetidin-2-one

HRID 867577Notes

Reaction equation

HRID 867577 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+]>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

4

Reactant 2

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

Product 1

HCID 13104623N-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-azetidin-2-oneYield 45.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)-2-azetidinone (1.94 g, 7.15 mmol) is dissolved in anhydrous methanol (20 ml) cooled to 0° and a solution of NaOMe (0.36 mmol) in MeOH (0.5 ml) is added to the mixture stirred at 0° for 2 hours. HOAC (0.1 ml) is added the mixture is evaporated under vacuum and the residue is taken up in CH2Cl2 ; washed with water, 5% NaHCO3, dried and evaporated to a pale yellow oil This is chromatographed on silica gel using EtOAc as eluant, to give 1-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-2-azetidinone 0.743 g (45%).

Workup

  1. temperaturecooled to 0°
  2. additionHOAC (0.1 ml) is added the mixture
  3. customis evaporated under vacuum
  4. washwashed with water, 5% NaHCO3
  5. customdried
  6. customevaporated to a pale yellow oil
  7. customThis is chromatographed on silica gel

Sources & evidence

ORD record
ord-54b6032fa2ef4c4a90b89d392b01ade6
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

Loading…