Acetaldehyde → Benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

HRID 620420Notes

Reaction equation

HRID 620420 reaction equation
[C:1]1([CH3:29])[C:2]([S:7]([O:10][C:11]2[CH2:17][CH:16]3[N:13]([C:14](=[O:18])[CH2:15]3)[C:12]=2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C([N-]C(C)C)(C)C.[Li+].[CH:38](=[O:40])[CH3:39].[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[OH:40][CH:38]([CH:15]1[C:14](=[O:18])[N:13]2[CH:16]1[CH2:17][C:11]([O:10][S:7]([C:2]1[C:1]([CH3:29])=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:9])=[O:8])=[C:12]2[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[CH3:39]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 131712683Benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 131712684Benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (41 mg) in anhydrous THF (0.5 ml) is added dropwise over 5 mins to a stirring solution of lithium diisopropylamide (from 15.5 μl of diisopropylamine and 0.07 ml of 1.6N BuLi) in anhydrous THF (1.5 ml) at -78°. The resulting solution is stirred at -78° for 10 mins and then treated with acetaldehyde (56 μl). After 5 more mins, saturated aqueous NH4Cl solution (1.5 ml) is added and the mixture is allowed to warm to room temperature. The mixture is diluted with ethyl acetate (20 ml), washed with H2O and brine, dried with MgSO4, filtered, and evaporated in vacuo to provide benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate as a mixture of diastereomers.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b548e009dc2349f8943dd2dd2d0e6da2
Source dataset
uspto-grants-1989_04
Patent number
US04820817

Reaction notes

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