Methanol → HCID 13505929, compound

HRID 1903016Notes

Reaction equation

HRID 1903016 reaction equation
[CH:1]([N:14]1[C:17](=[O:18])[CH2:16][CH:15]1[C:19](OCC)=[O:20])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O>C(OCC)(=O)C>[CH:1]([N:14]1[CH:15]([CH2:19][OH:20])[CH2:16][C:17]1=[O:18])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 20467706HCID 20467706, compound

Product 1

HCID 13505929HCID 13505929, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.3 g. (4.2 mmoles) of ethyl 1-benzhydryl-4-oxo-2-azetidine-carboxylate in 5 ml. of methanol 0.32 g. (8.4 mmoles) of sodium tetrahydrido-borate(III) are added with outer cooling with ice water and stirring. The mixture is stirred for 10 minutes, whereupon it is poured onto 20 ml. of water and shaken with three 10-ml. portions of ethyl acetate. The ethyl acetate solution is dried with magnesium sulfate, filtered and the filtrate is evaporated. The oily residue is crystallized by trituration with 10 ml. of ether. 0.82 g. (73%) of the named compound are obtained, melting at 101° to 102° C. (ethyl acetate/petroleum ether).

Workup

  1. stirringThe mixture is stirred for 10 minutes, whereupon it
  2. additionis poured onto 20 ml
  3. dry with materialThe ethyl acetate solution is dried with magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. customThe oily residue is crystallized by trituration with 10 ml

Sources & evidence

ORD record
ord-72c6903776f74d618a5959ab9f401dbc
Source dataset
uspto-grants-1984_03
Patent number
US04435322

Reaction notes

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