Acetaldehyde → HCID 56984832, compound

HRID 2290992Notes

Reaction equation

HRID 2290992 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:16]=1[CH2:17][N:18]1[C@H:21]([C@@H:22]2[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]2)[CH2:20][C:19]1=[O:29].[CH:36](=[O:38])[CH3:37]>CCCCCC.O1CCCC1>[CH3:13][O:14][C:15]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:16]=1[CH2:17][N:18]1[C@H:21]([C@@H:22]2[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]2)[C@@H:20]([C@H:36]([OH:38])[CH3:37])[C:19]1=[O:29]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 7912DiisopropylamineHCID 56615901HCID 56615901, compoundHCID 178418339Butyllithium

Product 1

HCID 56984832HCID 56984832, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

0.65 ml of a 1.7M solution of butyl lithium in hexane is added to a solution, cooled to -65°, of 111 mg (1.1 mmol) of diisopropylamine in 4 ml of tetrahydrofuran. The mixture is cooled to -78° and treated after 15 minutes with a solution of 321 mg (1 mmol) of (S)-1-(2,4-dimethoxy-benzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone in 1 ml of tetrahydrofuran. The mixture is stirred at -78° for 45 minutes and then a solution of 100 mg (2,27 mmol) of acetaldehyde in 0.5 ml of tetrahydrofuran is added dropwise within 3 minutes thereto, whereby the temperature rises to -70°. The mixture is stirred for 10 minutes, the cooling bath is removed, the reaction solution is treated with 2 ml of 14 percent aqueous ammonium chloride solution and extracted with 30 ml of ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated in vacuo. The residue is chromatographed on 10 g of silica gel with ethyl acetate/hexane (2:1) as the eluent. There is obtained (3S,4S)-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(R)-1-hydroxyethyl]-2-azetidinone which is obtained as fine needles of melting point 145°-146° after crystallization from ethyl acetate/hexane.

Workup

  1. temperatureThe mixture is cooled to -78°
  2. customrises to -70°
  3. stirringThe mixture is stirred for 10 minutes
  4. customthe cooling bath is removed
  5. additionthe reaction solution is treated with 2 ml of 14 percent aqueous ammonium chloride solution
  6. extractionextracted with 30 ml of ethyl acetate
  7. washThe organic phase is washed with saturated sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo
  10. customThe residue is chromatographed on 10 g of silica gel with ethyl acetate/hexane (2:1) as the eluent

Sources & evidence

ORD record
ord-94d56f4415df41b799a03aa599368e4a
Source dataset
uspto-grants-1986_10
Patent number
US04619787

Reaction notes

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